Real Estate Rookie Podcast

Episode: 10 Things You NEED as a DIY Landlord (Self-Managing Rentals)
Hosts: Ashley Kehr & Tony J Robinson
Date: October 15, 2025

Overview

This episode of Real Estate Rookie breaks down the 10 essential tools and systems every DIY landlord needs to self-manage rentals effectively and avoid the pitfalls of burnout, disorganization, or legal/financial missteps. Ashley Kehr and Tony J Robinson blend their hands-on experience with real-world anecdotes, practical resources, and advice for every rental strategy—long-term, mid-term, and short-term. Whether you own one door or a growing portfolio, this episode delivers a comprehensive toolbox to simplify property management for landlords at the start of their journey.

Key Discussion Points & Insights

1. Property Management Software ([00:51])

• Why Software is Essential:
  Ashley described her early experience working at an apartment complex tracking rent with pen and paper and how it led to chaos and inaccuracies. Their message: software brings accuracy, saves time, and builds bulletproof records.
• Short-Term vs. Long-Term Applications:
  Tony emphasized a PMS (property management system) is critical:
  • “For the hotel, we’re on websites I’ve never even heard of…and instead of logging into all these platforms, we're able to communicate with everyone through one unified inbox.” ([02:18])
  • Uses PMS for guest/vendor communication, calendar management, maintenance notifications, and inventory.
• Favorite Platforms:
  • Long-Term Rentals: Ashley recommends RentRedi and TurboTenant for small portfolios, AppFolio and Buildium for 50+ units.
  • Short-Term Rentals: Tony uses Hospitable (cost-effective), Guesty (for scale), and mentions Hostfully, Breezeway (for back-of-house and cleaning), and Turno (cleaner coordination).
  • For Flipping: Limited dedicated software aside from Excel, FlipperForce, and BuilderTrend.

Memorable Quote:

“You don’t want to have to do this with pen and paper—accuracy and time savings are critical, especially when there’s a dispute on rent paid.” —Ashley ([01:20])

2. Reliable Vendor List ([10:00])

• Building and Tracking Vendors:
  They both use project management boards (like Monday.com) and spreadsheets to track vendors, their services, and performance.
  • Ashley sorts vendors by type, reference, and outcome, even adding details like which vendors work 24/7.
  • Tony insists on the value of referrals and proactively reaching out to vendors in advance, not waiting for an emergency.

Notable Advice:

“Sometimes it makes sense, even if you overpay a little, just to go back to that person that's more consistent … overall, it’s a positive win-win.” —Tony ([15:11])

3. Separate Contact Number ([18:58])

• Boundary Setting:
  Both recommend using Google Voice (free or low-cost), providing a dedicated phone line for tenants, vendors, and business inquiries—keeping your personal number private and your VA/team connected.
  • Tony also trials OpenPhone with more advanced call routing and call recording for quality control.
• Oversight:
  Ashley likes being able to log in and see call history, voicemails, and text transcripts for team supervision.

Memorable Moment:

“My recommendation: Google Voice ... so I don’t end up with two phones or my number all over spam lists.” —Ashley ([19:02])

4. Virtual Mailbox ([24:41])

• Mail Management Game-Changer:
  Ashley explained how a virtual mailbox streamlined mail sorting, scanning, and check deposits, reducing clutter and saving significant time/cost versus hiring staff.
  • All mail can be sorted, shredded, scanned, and forwarded from anywhere.
• Cost:
  Plans are ~$300/year, scalable for multiple LLCs.

Anecdote:

“I've literally been telling Tony about this for two years because I saw the picture that Sarah had posted of him covered in a pile of mail...” ([31:42])

5. Organized File Storage ([31:42])

• Digital Organization:
  Both hosts now use Google Drive for all records—leases, receipts, bank statements, closing docs—with easy folder access and backup, plus cross-linking in project management software.
  • Prepares for lender requests and makes transitions between software seamless.
  • Ashley recommends always scanning and saving even “one-off” documents.

6. Unit Information Sheet ([36:33])

• Centralized Property Info:
  Maintain a cheat-sheet per property with critical details: location of shutoffs, vendor contacts, utility info, video walkthroughs, and access codes.
  • This saves hours during crises or when relaying info to teammates or vendors.
• Resource:
  BiggerPockets offers a template: biggerpockets.com/rookieresource

Memorable Tip:

“As you accumulate a few properties, they kind of blend together... a little organization up front saves you hours of headaches later.” —Ashley ([40:05])

7. Emergency Fund / Reserves ([43:12])

• Financial Cushion is Non-Negotiable:
  Keep 3–6 months of reserves, ideally in a high-yield savings account (Ashley uses Baselane and Wealthfront, Tony uses Relay).
  • Don’t treat projected cash flow as profit—prioritize replenishing reserves after any dip.
• Short-Term Rental Reinvestment Fund:
  Tony recommends a separate fund for continuous improvements, inspired by resort practices.

8. Insurance & Legal Protection ([47:26])

• Landlord Insurance ≠ Homeowner’s Insurance:
  Don’t rely on homeowner policies; get landlord or STR-specific policies. Consult agents to understand all coverage, deductibles, and exclusions.
• Annual Policy Review:
  Tony suggests shopping around each year for better rates or new options—don’t just “set and forget.”
• Specialized Coverage for STRs:
  Ashley highlights features such as bedbug coverage, lost rents, squatter/eviction, liquor liability, and amenity (pool, hot tub) coverage. Always openly disclose property uses and amenities to fully protect yourself.

Warning:

“What’s the point of having insurance if you’re not going to have the right coverage?” —Ashley ([52:56])

9. Communication Boundaries & Systems ([53:51])

• Set Expectations:
  Define how and when tenants, guests, vendors, or staff can reach you. Establish what constitutes an emergency versus routine communication.
  • Use PMS for non-urgent requests.
• Guest Communication:
  For STRs, use automated info, digital guidebooks, signage, and proactive FAQs to drastically reduce late-night or unnecessary calls.
  • Tony shared adding a light and instructional signage by keypad doors to solve frequent lockout calls.

Quote:

“If we can just eliminate the need altogether, it's a win-win because the guest never has to reach out, which means everything went smoothly.” —Tony ([59:46])

10. Plan for Scaling Beyond DIY ([60:08])

• Systems & Processes:
  Ashley stresses SOPs, checklists, financial reserves, and capital as the foundation for scaling. Build checklists for every repeatable task to streamline onboarding, acquisitions, or outsourcing.
  • Even if you enjoy certain tasks, automate or document to free up time and reduce mental load.
• Finding What to Outsource:
  Tony describes bottom-up business building: you do everything first, then delegate lowest-value tasks as resources/free time allow.
• Book Recommendations:
  1. The Checklist Manifesto by Atul Gawande
  2. Clockwork by Mike Michalowitz

Key Takeaway:

“What are the things I should be focusing on versus the things that I shouldn't be focusing on?... That’s how you lay the foundation for scaling well.” —Tony ([63:59])

Notable Quotes & Memorable Moments

• "It’s about having the right systems, tools and backup in place so you don’t lose your sanity." —Ashley ([00:00])
• "People are much more willing to share their plumber than their wholesaler!" —Tony ([12:08])
• "I used to be unorganized, it would take me forever to find what I needed for the loan officer. Now I just click through Google Drive and my links." —Ashley ([34:52])
• "The more experienced flippers we know…still use Excel for their scope of work." —Tony ([09:07])
• "I can't even tell you how many times I got maintenance requests at 1am, not an emergency, just someone remembering their outlet isn't working." —Ashley ([53:51])
• "You are the team—you are operations, you are HR, you are acquisitions." —Tony ([63:59])

Timestamps for Key Segments

• Property Management Software: 00:51 – 09:07
• Vendor List & Relationship Management: 10:00 – 16:13
• Separate Contact Number: 18:58 – 24:34
• Virtual Mailbox: 24:41 – 31:42
• File Storage: 31:42 – 36:33
• Unit Information Sheet: 36:33 – 40:05
• Emergency Fund: 43:12 – 47:26
• Insurance: 47:26 – 53:51
• Communication Boundaries: 53:51 – 60:08
• Scaling Beyond DIY: 60:08 – 66:33

Final Thoughts

Ashley and Tony provide a pragmatic, approachable roadmap for rookie landlords. The focus isn’t on 10X-ing overnight but on building a modest, well-run portfolio with smart systems and relationships. Their advice is relatable, rooted in their own rookie blunders and hard-won lessons, making it invaluable for anyone managing their first properties on their own.

Resource Links

• BiggerPockets Rookie Resource

Hosts on Social:

• Ashley: @wealthfromrentals
• Tony: @tonyjrobinson