Relocation in Retirement

Summary

Jill on Money with Jill Schlesinger

Episode: Relocation in Retirement

Date: July 29, 2026
Host: Jill Schlesinger, CFP®
Co-host: Mark

Episode Overview

In this episode, Jill Schlesinger takes listener questions focused on retirement decisions, particularly the financial and emotional considerations of relocating after retirement. The show covers the complexities of moving for tax benefits, consolidating investment accounts, long-term care planning alternatives, escaping timeshares, annuities in later life, and proper document retention. Jill and Mark bring their signature straightforward, jargon-free analysis to help listeners make practical choices, balancing financial optimization with quality-of-life considerations.

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Key Discussion Points & Insights

1. Relocating in Retirement for Tax Reasons

• Listener Question: Deborah (66, Oregon) feels trapped in her current situation: she has a solid pension, sizable 457 plan, and is considering moving to Washington or Nevada to avoid Oregon's 10% tax on 457 withdrawals. Her elderly mother in Oregon also needs her care.
• Jill’s Take (02:17–06:10):
  • Relocation for purely financial reasons is not always worth it, especially when family and emotional ties are involved.
  • Even though reducing a 10% tax can be appealing, the upheaval and distance from her mother may not justify the move.
  • Encourages listeners to consider their actual expenses and quality-of-life factors, not just the math.
  • Notable Quote:

    "I usually don't like to say go move because of money because that's also kind of weird...the other part of it is just being trapped because of just kind of your life stage." — Jill (03:26)

• Mark’s Perspective (05:39–06:10):
  • Relates to people living in high-tax places and never considering moving solely for taxes.
  • Suggests staying if the listener enjoys her home and community.

2. Consolidating Investment Accounts

• Listener Question: Mary wants to simplify multiple taxable accounts with large gains by transferring them “in kind” but doesn’t want to trigger taxes by selling.
• Advice (06:10–07:55):
  • Jill is in favor of “in kind” transfers for the sake of simplicity, as long as asset allocation remains safe.
  • Selling isn't necessary unless your asset allocation is lopsided (e.g., all in stocks).
  • Mentions donor-advised funds as a way to put appreciated assets to charitable uses while getting a tax deduction.
  • Notable Quote:

    “If you held funds in different places...and you want one basic taxable account, move it into one. Pick one place where you want these assets to live.” — Jill (07:27)

3. DIY Long-Term Care Fund vs. Insurance

• Listener Question: Roger didn’t buy long-term care insurance 20 years ago, instead investing $1,000/month; now has $500,000 earmarked for care and wonders if his children (in their 30s) should follow this approach.
• Advice (07:55–10:19):
  • Jill suggests that children in their 30s do not need to plan as aggressively for long-term care now.
  • Notes long-term care insurance is complex and not always a fit for younger people.
  • Alternative strategies: Health savings accounts, separate investment accounts, or possibly work-sponsored long-term care.
  • Notable Quote:

    “...if they have long-term care insurance offered as a benefit through work, that's another way to think about it.” — Jill (09:29)

4. Getting Out of a Timeshare

• Listener Question: Bernadette and her husband regret buying a timeshare and seek guidance on exiting.
• Memorable Moment (10:19–11:01):
  • Mark invokes Jill’s late mother-in-law’s wisdom:

    “Yeah, timeshares are for suckers.” — Mark (10:59)

• Jill’s Advice (11:05–11:46):
  • Confirms timeshare contracts are notoriously difficult to escape due to ongoing maintenance fees.
  • Suggests consulting an attorney and warns against “walk away” schemes without full understanding.
  • Discusses options like gifting (with skepticism), and reiterates: “Don’t buy a timeshare. I don’t care who you are, don’t buy them.”

5. Annuity Products vs. Safer Portfolios in Older Age

• Listener Question: Susan (73) considers switching her investment account to an annuity with guarantees after experiencing the 2008 recession.
• Advice (11:48–13:34):
  • Jill advocates evaluating risk reduction within a traditional portfolio (e.g., a bond ladder) rather than shifting to an annuity product, which often has hidden costs.
  • Suggests seeking a second opinion before initiating annuity transactions.
  • Notable Quote:

    “Instead of converting a stock portfolio into an annuity portfolio, I wonder if you could...just be buying some individual bonds so even if the value fluctuates, you have a bond ladder.” — Jill (12:12)

6. How Long to Keep Financial Documents

• Listener Question (“R.”): Seeking clarity on best practices for record-keeping.
• Advice (13:30–14:37):
  • Only tax returns and supporting documentation need to be stored for 6–7 years.
  • Other records (bank, investment, utility statements) can generally be shredded after 30 days—unless needed for tax reasons.
  • Mortgage documents should be kept while you have the mortgage; shred after payoff.
  • Notable Quote:

    “Get them electronically so you don’t even have to shred them.” — Jill (14:31)

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Timestamp Highlights

• 02:17–06:10 — Facing the emotional side of relocating for tax reasons in retirement.
• 07:27–07:55 — Step-by-step on consolidating investment accounts “in kind.”
• 10:59–11:01 — “Timeshares are for suckers.” (Mark, quoting Jill’s late mother-in-law)
• 12:12–13:34 — Risk reduction with bond ladders vs. costly annuities.
• 14:31–14:37 — On going paperless with financial statements.

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Memorable Quotes

• “When is my shake up the snow globe moment going to arrive? I retired six years ago. I’m feeling that retirement is treading water and taking care of my mom.” — Listener Deborah (03:15)
• “If you like Oregon, if you love your home, if you love your community, I would stay there.” — Mark (05:53)
• “If you’re charitably inclined, you could open up a donor advised fund...you can shove it into that, you can contribute it into a donor advised fund, you can get a big tax write off...” — Jill (07:46)
• “Long-term care is really rough because it has...a lot of moving parts to it. Maybe they won’t need it because they’ll inherit all your money.” — Jill (09:15)
• “Don’t buy a timeshare. I don’t care who you are, don’t buy them, they’re bad.” — Jill (11:48)
• “Get them electronically so you don’t even have to shred them.” — Jill (14:31)

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Takeaways for Listeners

• Relocating for tax reasons is complex—factor in emotional and familial connections, not just dollars.
• Consolidate investment accounts to simplify management, but don’t let fear of taxes block needed diversification or rebalancing.
• DIY long-term care funds worked for some, but insurance is rarely needed for people in their 30s.
• There are no easy outs for timeshares—consult an attorney and proceed with caution.
• Reducing investment risk as you age doesn’t have to mean expensive annuities—consider simple portfolios with bonds.
• Keep tax records for 6–7 years; shred most other financial paperwork much sooner. Go digital to save space and stress.

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Tone & Closing

Jill and Mark maintain their approachable, candid, and sometimes irreverent style, clarifying that financial decisions are not just mathematical but deeply personal. They invite listeners to reach out with their questions, reinforcing the community aspect of the show:

“If you want that combo, bring it. Get in touch with us.” — Jill (16:10)

The episode is an insightful and accessible listen for anyone navigating retirement choices, family responsibilities, and day-to-day financial management.

Transcript

[Jill]

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Welcome to the Jill on Money show. It's Wednesday, July 29th, and we are here answering your financial questions. If you've got one, just shoot us a note. Go to jillonmoney.com, click the contact Us button, write down what's on your mind and if you want to say something really nice just about Mark and the show. Not me necessarily, but Happy to have you do that. Otherwise you can always leave a rating and review wherever you listen, there's that too. But if you've got a question about something going on for you, maybe a choice you have to make, maybe it's just that you're kind of feeling uneasy about a situation and you just want someone else to weigh in, someone who's got a certified financial planner designation. Both Mark and I have that. Get in touch with us. Go to jillonmoney.com click the contact us button, write us a note, check the box if you want to come on the air. We're going to do some emails today because we don't like when things kind of get socked into that box and things pile up too much. So let's try this one. Let's start with Deborah, who says, I am 66 and currently living in Oregon with a pension of $3,700 a month. I have not yet claimed social because Oregon taxes all retirement aside from Social Security and Estates over $1 million. Should I move to Washington or Nevada to finish my retirement? Social Security at my full retirement age would be 2465. A month, she says. Goes on to say, I'm feeling a little bit trapped right now as my 89 year old mom who needs my assistance with some things has some serious health issues. My siblings are out of state and one out of the country. When is my get this ready for this Mark? I never heard this, but I love it. When is my shake up the snow globe moment going to arrive? I retired six years ago. I'm feeling that retirement is treading water and taking care of my mom. I can't take extra money out of my 457 for anything without a 10% tax from Oregon being slapped onto it. Help. I'm single, no kids and there's 800 grand in the 457 plan. Well, I mean, this is kind of a tough situation. I usually don't like to say go move because of money because that's also kind of weird. On the other hand, are you willing to, I mean, is it o could you do that? I mean, obviously it would be better, but could you move away from your mom? You know, I don't know. The one thing you didn't actually talk about was what your actual expenses are if you could move. Okay, let's say you're in Oregon and you're living in Portland. You're like, oh, I can move to Washington state and still be close enough to my mom to do that. Sure, that's fine. But the other part of it is just being trapped because of just kind of your life stage. And I get this, Marc. We've heard from a lot of people. They're stuck in the middle of situations like this. What do you think, Mark, about moving out of state to reduce the 10% tax? I mean, 10% is not that much, but it's not a small amount either. I don't know how much she really would need to take out of the account.

[Mark]

Yeah, I mean, we obviously have questions. She's got a nice pension. That's a real number. 3,700amonth. She hasn't turned on Social Security yet. I'm guessing that's probably at minimum three grand a month. So I don't know. What?

[Jill]

Well, she said Social Security will be 2465. Yeah, 2,500.

[Mark]

So, yeah, I don't know what she spends, but, you know, the thought of moving somewhere for a tax benefit, it's not something I can wrap my head around. I mean, you know, New York sucks for taxes, but never in a million years would I consider moving elsewhere to improve my tax situation. If she likes Oregon, if she loves her home, if she loves her community, I would stay there.

[Jill]

I would, too. Especially if it's like, oh, this is also where my mom is. That's the other part of it. If you feel like, you know, in terms of your own life, that if you turned on your Social Security and you had that six grand a month, then maybe, just maybe, you stay where you are and that can help you out. But we need a little bit more information. But I get that issue. I really do. But I've never heard the term shake up the snow globe moment, which I love. So thank you for introducing that to us. Okay, Mary says we're spread out over several different mutual fund families. Would it be smart to do an in kind transfer to consolidate and simplify? We have several taxable accounts with big gains over the years, and we don't want to sell them now. As we age, we would like to keep things simple, but what can they do? Okay, so here's the thing. The first thing I would say is, if we're just talking about consolidating an account. I love this idea. So in other words, if you held funds in different places, all over the place, and you want one basic taxable account, move it into one. Pick one place where you want these assets to live. So, you know, maybe it's Schwab, and maybe it's Fidelity, and maybe it's E Trade.

Whatever it is.

Put them in one place. When you're talking about big gains over the years and that you don't wanna sell them, maybe you don't have to. I don't know what you're, I don't know what we're talking about. But presumably if you were just talking about consolidation, I'm all in. Do it, Absolutely do it. But the idea of not selling something because of the taxes, if that means that you're like 100% in stocks and stock index funds because of this, then I might change my, my tune also. I don't know how old you are, but there's a couple of other things that you can be thinking about. Like if you're charitably inclined, you could open up a donor advised fund. And I love these things. You can take a low basis position and fund as you're talking about, you can shove it into that, you can contribute it into a donor advised fund, you can get a big tax write off in the year that you do it and then you can give the money out over time. So I would definitely think about doing that, Mary. And you know, I think cleaning things up makes a lot of sense. I really do. Okay, Mark, here's the next one. This is from Roger. Twenty years ago, my wife and I went shopping for a long term care insurance policy. The plans that were presented had a benefit of about $450,000. But you had to go through all of the medical insurance, the Medicare, and we would need certification from doctors that long term care was necessary and there was no level premium guaranteed. We did not like the terms of the plans. We decided to invest $1,000 a month into a brokerage account earmarked for long term care. Listen to this, Mark. Now that we're 65 years old, in good health, our long term care account is worth close to a half a million dollars. Hindsight being 20 20, we think we made a good decision at the time. But should we recommend this strategy for our children who are in their late 30s? Listen, first of all, your kids are in their late 30s. No, you don't need to do that. Second of all, each of your kids has a somewhat different long term care outlook. And I certainly would, I would absolutely not be interested in spending the ton of money for a long term care policy for them. But if you're saying, hey, you know what, you should have a little bit of money that's set aside, either it's a health savings account, maybe that's something they should look into. It's a brokerage account, maybe that's something they should look into. Or if they have long term care insurance offered as a benefit through work, that's another way to think about it. So that to me is, you know, it's a complicated question. Long term care is really rough because it has. There are a lot of moving parts to it. Maybe they won't need it because they'll inherit all of your money. So think of it that way. Mark, I would like you to try to channel my dearly departed mother in law when I tell you the subject of this next email.

Are you ready?

[Mark]

Ready.

[Jill]

Okay, Bernadette, subject timeshare exit. Let me read you the email and then you can quote my mother in law. She says, my husband and I made a stupid decision. We were coerced into signing a timeshare agreement. It is haunting us because since entering this agreement, we have faced some unfortunate challenges with our finances and physical mobility. What is your advice on how to exit a timeshare? Are you familiar with lawyers that can be trusted to help us? Mark, what did my mother in law say to my brother in law when he said he bought a timeshare?

[Mark]

Yeah, timeshares are for suckers.

[Jill]

Thank you, Marie.

[Mark]

So not to say that Bernadette's a sucker.

[Jill]

No.

But you know what these are, these contracts are rough. So there are. We have run across people who have found these services to help sell them. Here's the thing. You can walk away from it. It's just that you're on the hook for these annual fees, these maintenance fees. And the question is, is there a way out of that? And the answer is, I don't know someone who does it specifically, but I am very, I'm very worried that you just like walk away with it without understanding what the legal obligation is. So I would talk to an attorney about it. Maybe, I don't know. Mark, can you gift them? Can you just like, you know, put it on someone else? What do you think?

[Mark]

Yes. Some gift that is.

[Jill]

I know a charity. I don't know. It's tough. They're terrible. Don't buy a timeshare. I don't care who you are, don't buy them. They're bad. Susan writes she wants to know about annuities. I'm 73 years old. I'm trying to work on whether to change a investment account into a more stable portfolio. So growth is not my issue at this point. I have been offered a and annuity with certain with surety benefits. I've never heard of this. I've been through the recession back in 2008. I don't feel like I have the time to go through something like that again. Any suggestion you might give me would really be helpful. So look, instead of converting a stock portfolio into an annuity portfolio, I wonder if you could just. And maybe it sounds to me I know the name of the firm that you. You gave us the name of the firm. I didn't say it, but like, it sounds like you probably have a broker involved. You can say to this person, could I have less risk in this portfolio and could I just be buying some individual bonds so even if the value of the bonds fluctuates, that I have a bond ladder and they come due every so often, one year, five year, 10 year. And that way you will not be on the stock market roller coaster. You know, I think that index annuities, they're hot commodities right now because people are worried, like, oh, what happens if the stock market craps out? But these annuities always have costs, so we'd want to really look at that annuity. And if you are interested in an annuity, what I might do is go to another advisor and get a second opinion.

[Mark]

Yeah. Because she says growth is not the issue. So it sounds like she's got what she needs.

[Jill]

Yeah. So, you know, you could just buy. You could build a bond ladder and I don't know how much money she has, but you know, that's, that's important. Okay, now, last question mark. This is from someone who has a recognizable name. So I'm just going to say R. Subject is documentation. I know you talked about it one morning on CBS Mornings. You said to hold on to bank statements for seven years and no, come on, pay attention, everybody. Okay, so this is all about, like, documentation. Okay, so here's what you need to hang on to for seven years. It's six or seven years is tax returns. That's it. The other stuff you don't need, bank statement, bank statements and utility bills. You can shred these things after 30, 30 days or something. The only reason you keep a bank or an investment statement longer is if there is a tax purpose associated with it. Phone bills, utility bills, Pay them, shred them, pay them, shred them. And by the way, get them electronically so you don't even have to shred them.

[Mark]

What about old mortgage docs?

[Jill]

Well, you can hold your mortgage document as long as you have a mortgage. Once the mortgage is paid off, get rid of it. It's done. Now all the documents that are associated with things you have still hold onto them. And you Know, obviously wills and powers of attorney and all that stuff. You know, it's weird, Mark. I just came across my grandfather's estate tax settlement. I don't know why I had it. It just was in, like, I think it was in my dad's files. But, you know, mostly once you get past seven years or something, just like shred it all unless you want it for post, but that's it. I don't know, like, the whole tax thing, it's almost like inconceivable to me that you have to hang onto them that long, but you do. 6. It's really 6. Ish. If you want to call it 7, you can call it 7. Another fine show, Mark. Are you excited to be wrapping up today for this great show? I hear it in your voice.

[Mark]

Highlight of my week, Jill on Money.

[Jill]

The highlight of my week is talking to you, Mark. Every single time. Every time. I just love it. It's like my. It's like my. I like to think of us as sort of siblings, but I'm your much older sister, not really your aunt. I don't feel like I'm an aunt.

Do you?

[Mark]

12 years older.

[Jill]

It's a lot.

[Mark]

Not really.

[Jill]

I'm old. I don't know. It kind of is. Anyway, you're much older sister. That's what I got. All right. Hey, gang, do you want your siblings, Mark, Aunt Jill and Uncle Mark, brother Mark, sister Jill. If you want that, you want that combo, bring it. Get in touch with us. Go to jillonmoney.com. click the contact us button if you want to come on the air.

Don't forget to check the little box

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Thank you for listening and we'll talk to you tomorrow.

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