Changing My Rent Strategy Represents a $20,000 Annual Opportunity

Joliet, Illinois
General Landlording & Rental Properties
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Changing My Rent Strategy Represents a $20,000 Annual Opportunity

Alison Robinson
Rental Property Investor · Joliet, IL · Member since 2013 · 102 posts · 48 votes

My rental portfolio was sitting at roughly 82% of market.

Moving from conservative pricing toward a moderate-aggressive pricing strategy has the potential to increase gross rental income by $20,000 annually.

I developed a Rent Estimator tool - It's a repeatable format that uses AI to research current market evidence, compare multiple sources, distinguish asking rents from stronger evidence such as leased properties, assess confidence, and produce a rent range.

The output also gives me several pricing levels, from conservative through aggressive.

It gives me another analysis to compare against the PM's recommended listing or renewal rent.

I'm still treating it as a support tool, not the decision maker. Market data can be incomplete, comparables aren't always comparable, and AI can certainly get things wrong.

For other small portfolio owners: how are you determining market rent today?

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Twannisha Jackson
Rental Property Investor · Cleves · Member since 2023 · 132 posts · 82 votes
1mo

hi, I look up fair market rents, rents from zillow, craigslist, yard signs, etc. I read somewhere that tenants value location, in unit washer/dryer, pets & someone who will actually fix stuff & responds back asap. I also discuss rents with them, so far so good. it actually worked out better than expected when I went in for a rent increase- they gave me more than I asked. they’re good folk.

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  • Richard F.
    Honolulu, HI · Member since 2008 · 3k+ posts · 2k+ votes
    1mo

    Without pics of the competition, interior AND exterior, the numbers are marginally useful. Apparent condition and style certainly affect not only the value of the unit, but the quality of prospects.

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    • Alison Robinson
      OP
      Rental Property Investor · Joliet, IL · Member since 2013 · 102 posts · 48 votes
      1mo

      Condition can be a big differentiator in rent, particularly for rentals at either end of the condition spectrum.

      The methodology used by the Rent Estimator follows an approach commonly used by online rent-estimation systems: property characteristics, location and comparable rental data. Certainly, the more information you can provide about the property and the comps, the better the analysis. That's also one of the reasons a property manager's local experience can be valuable.

      What approach have you found reliable for establishing market rent?

      0Reply
  • Twannisha Jackson
    Rental Property Investor · Cleves · Member since 2023 · 132 posts · 82 votes
    1mo

    hi, I look up fair market rents, rents from zillow, craigslist, yard signs, etc. I read somewhere that tenants value location, in unit washer/dryer, pets & someone who will actually fix stuff & responds back asap. I also discuss rents with them, so far so good. it actually worked out better than expected when I went in for a rent increase- they gave me more than I asked. they’re good folk.

    1Reply
  • Joseph Zimmerman
    Investor · Chicago · Member since 2026 · 17 posts · 12 votes
    1mo

    With enough time before a vacancy, I price at premium market rates based on comparables and then service the unit with premium care and urgency on any issues.

    Self-managing can be difficult at times, but also allows me to provide the best possible offering to someone in my unit. It also adds a personal touch that tenants appreciate.

    On the backend, I track every expense in my custom P&L to ensure that my KPIs are still positive despite of all the service visits.

    1Reply
    • Alison Robinson
      OP
      Rental Property Investor · Joliet, IL · Member since 2013 · 102 posts · 48 votes
      1mo

      Joseph,

      I like how you connect premium pricing with premium service rather than treating rent as a standalone decision.

      The part that really caught my attention is your custom P&L and KPIs. I tend to look at rent strategy through cash flow, vacancy, maintenance, and retention, so I’d be interested in how you measure whether the premium-service model is actually producing a better financial outcome.

      What KPIs have you found most useful? I’d also be interested in comparing notes on KPIs, portfolio performance, and strategy if you are.

      1Reply
    • Joseph Zimmerman
      Investor · Chicago · Member since 2026 · 17 posts · 12 votes
      1mo
      Quote from @Alison Robinson:

      Joseph,

      I like how you connect premium pricing with premium service rather than treating rent as a standalone decision.

      The part that really caught my attention is your custom P&L and KPIs. I tend to look at rent strategy through cash flow, vacancy, maintenance, and retention, so I’d be interested in how you measure whether the premium-service model is actually producing a better financial outcome.

      What KPIs have you found most useful? I’d also be interested in comparing notes on KPIs, portfolio performance, and strategy if you are.

      I track maintenance and CapEx as a share of collected rent on each property every month in my custom P&L, and I run both against the assumptions I underwrote the deal on. My original numbers carried 5% vacancy, 5% maintenance and 5% CapEx, so the monthly question is whether the premium-service spend is staying inside that reserve or eating into it.

      I also keep realized cap rate, DSCR and cash-on-cash per property. DSCR is the one that moves most, because the standard calculation leaves CapEx out and my all-in number after actual CapEx is meaningfully lower.

      On the pricing side, I watch the spread between in-place rent and the current market estimate. A wide spread is turnover risk. At re-lease I have to defend that gap against the market estimate. This is usually a gut-feel on tenant satisfaction by staying in contact with them.
      0Reply
  • Alan T.Pro Member
    Rental Property Investor · Member since 2019 · 16 posts · 3 votes
    1mo

    You can do this quite easily in chatgpt or claude. Set up a scheduled check so it can look at your open listings, and see how its doing agains the market.

    The trick is seeing what listings are being filled... its one thing to think your pricing competitively, but recognizing the price point at which other listings are being filled is whats going to help you the most in figuring out your comps. Further, it can be difficult to do a apples vs apples comparison without either looking at the listing yourself, or having AI do it. e.g. antother rental might have a move in special, 1 month free etc depending on market, and you wont see that by just browsing prices. We use rentometer as an example of one of the datapoints we use(not in the way you might think), but that for sure hides a lot of these nuances.

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