What's one thing you tried to automate in your rentals that didn't work?
Technology · Vancouver, BC · Member since 2026 · 261 posts · 67 votes
What's one thing you tried to automate in your rentals that didn't work?
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Member since 2023 · 177 posts · 61 votes
2dGood question, Lee, and your point about writing the process down first is exactly right. The thing that automates well for us is rent collection, but only because there is one payment method written into the lease, the same for every house. No exceptions, no chasing five different apps.
What never automated well for us: screening judgment and maintenance triage. Screening is verified repeatable income plus checking that the story matches the paperwork. No software does that consistency check for you. Same with maintenance: a tenant message still needs a person deciding whether it is a real emergency or a reset button and a two-minute call.
If I tried it again, I would automate the repeatable money movement first and keep a human on the decisions that cost real money when they go wrong.
22 Replies
- Member since 2023 · 177 posts · 61 votes2d
Good question, Lee, and your point about writing the process down first is exactly right. The thing that automates well for us is rent collection, but only because there is one payment method written into the lease, the same for every house. No exceptions, no chasing five different apps.
What never automated well for us: screening judgment and maintenance triage. Screening is verified repeatable income plus checking that the story matches the paperwork. No software does that consistency check for you. Same with maintenance: a tenant message still needs a person deciding whether it is a real emergency or a reset button and a two-minute call.
If I tried it again, I would automate the repeatable money movement first and keep a human on the decisions that cost real money when they go wrong.
- Technology · Vancouver, BC · Member since 2026 · 261 posts · 67 votes2d
I really appreciate you starting us off. One payment method written into the lease, the same for every house, is such a good example of why the process has to come first. It shows the software is only ever as good as the rule behind it.
I also like where you drew the line. Screening and emergency triage are judgment calls where a wrong answer costs real money, so keeping a person on those while the repeatable money movement runs on its own sounds like exactly the right split.
Great to hear how your team runs it,
Lee - 2dJohn RacinePro MemberRental Property Investor · Casselberry, FL · Member since 2008 · 234 posts · 119 votes
Lee, for me it was guest messaging. I tried two different AI-driven messaging tools, and neither one sounded like me out of the box. Much like training a new hire, I really had to get into the weeds to train it to my voice and style before I trusted it with guests.
If I did it again, I'd plan for that training time up front instead of expecting it to work on day one. Your point about writing the process down first applies here too: the more clearly you know how you answer the common questions, the faster the tool learns to answer them your way.
Even now, a person reads every thread and updates the responses whenever something changes at the property. Same with pricing. PriceLabs drives my rates, but I still review it every week, and pricing is still the task that takes the most of my time each month. The software does the work. It still needs someone checking it.
Disclosure: I co-host STRs for other owners.
- Technology · Vancouver, BC · Member since 2026 · 261 posts · 67 votes2d
Hi @John Racine,
"Much like training a new hire" is exactly the right way to see it. Nobody expects a new hire to sound like you on day one, so it makes sense that software can't either.
You also nailed the part most people skip. A person still reads every thread. The tool handles the volume, and you keep the voice and the judgment.
We found the same thing in our own businesses. The training time up front felt slow, and it's the part that paid for itself later.
On pricing, what does your weekly review actually look for? Local events, competitors dropping their rates, or something else?
Cheers,
Lee - 2dJohn RacinePro MemberRental Property Investor · Casselberry, FL · Member since 2008 · 234 posts · 119 votes
Thanks @Lee Futcher , it is multipronged. I use PriceLabs heavily so I start in my Market Dashboards. The data there is SOOOO rich, so that is ground zero. Actually put a recent video on my YT channel for that.
Then, I go into the individual properties and look at the Neighborhood data. There is hyperspecific info there I can glean insights from.
Then I go to my knowledge of the market and what I may know is coming. For example, before the NFL season, I flagged all my Jacksonville Jaguar home games so I get a premium for those weeekends. I'd like to say I saw their amazing season coming but I was prepared to flex down if I had to. Same with The Players Championship and a few other local events.
Did the same thing with my Lakeland property. Different market and different demograpghics but the same process. They have a big airshow type event in March looking at the things like that.
- Monroe, Orange County · Member since 2026 · 16 posts · 4 votes2d
Automated late-fee texts. On paper it was great: rent not in by the 5th, the fee posts and the tenant gets a message. In practice it fired on tenants whose bank transfer was already in flight, and on the one tenant who'd called me the week before to say they'd pay on the 8th. Two annoyed good tenants cost more than the fees ever brought in.
What works for me now: automate the reminder (a friendly note two days before and on the due date), but keep the late fee as a manual click after I've looked at who's actually late and why. The boring stuff gets automated, anything that feels like a penalty stays human.
- Technology · Vancouver, BC · Member since 2026 · 261 posts · 67 votes2d
Hi @Ezra Bennett and @John Racine,
Ezra, "anything that feels like a penalty stays human" is the best rule in this whole thread. Automate the reminder, keep the judgment. Two annoyed good tenants is exactly the cost nobody puts in the spreadsheet.
John, flagging every Jaguars home game before the season even started is the part no software does on its own. The tool brings the data. You bring what's coming to town.
You both landed in the same place. The system does the repeatable work, and a person makes the call that touches a real relationship.
Cheers,
Lee
- Real Estate Agent · Memphis · Member since 2026 · 632 posts · 363 votes2d
Automated maintenance scheduling is one that can easily backfire. A tenant submits a request, the system schedules a vendor, but nobody checks whether it's actually urgent or whether the vendor is the right fit. Suddenly you're dealing with unnecessary service calls and frustrated tenants. I'd keep the request intake automated but have someone review and approve the next steps before dispatching anyone. Some parts of maintenance just need human judgment.
- Member since 2026 · 1 post · 0 votes1d
The one I see fail most often is the phone. People forward the line to an auto-attendant or a voicemail-to-text tool, and tenants either hang up or press 0 until a human answers, so nothing was saved.
Two reasons it fails. First, one flow is asked to handle everything: leasing inquiries, rent questions, repairs and emergencies. Second, nobody wrote down what counts as an emergency, so the system either wakes you for a dripping tap or holds a no-heat call until morning.
What I'd do differently: start with one call type only, usually after-hours maintenance. Write the triage rules on one page (no heat, active water leak, gas smell, lockout). Anything on that list rings a person right away, and everything else becomes a ticket with the address and a callback window. Then listen to the first 20 or 30 calls yourself and fix the rules before adding a second call type.
Same lesson as Ezra's late fees: automate intake and reminders, keep the judgment with a person.
Disclosure: I'm the founder of Callers, an AI phone agent platform, so I see a lot of these setups.
- 1dAshish AcharyaBusiness MemberCPA, CFP®, PFS · Sarasota, FL · Member since 2017 · 5k+ posts · 3k+ votes
The one we see fail most from the accounting side is auto-categorized bookkeeping. Bank feeds and rules are great at sorting volume, but they can’t tell a repair from an improvement, and they’ll happily book the full mortgage payment as an expense when only the interest is deductible. Security deposits get coded as rent, and transfers between accounts get double-counted as income. By year-end the books look clean but the numbers are wrong, and cleaning it up costs more than the software ever saved.
What works is the same thing you described. Write down the rules first, like what counts as a capital improvement, how deposits get tracked, and how principal and interest get split, and then let the software apply them. Add a quick monthly review of anything over a set dollar amount instead of trusting every rule blindly. Happy to connect!
INVESTOR FRIENDLY CPA®4.9242 Reviews - Technology · Vancouver, BC · Member since 2026 · 261 posts · 67 votes1d
Great to see you, @Jim Johnson, @Rennen Chacham and @Ashish Acharya,
Jim, keeping intake automated and putting a person on the dispatch decision is a smart split. A system that books a vendor for a reset button is how a small request turns into a bill and an annoyed tenant.
Rennen, starting with one call type and writing the emergency list on one page is exactly the process first approach this thread keeps coming back to. Listening to the first 20 or 30 calls yourself is the step most people skip, and it's where the rules actually get good.
Ashish, I hadn't thought about the books, but it fits perfectly. Books that look clean but are wrong can be worse than messy ones, because nobody thinks to check them.
It's great to see the same lesson show up in maintenance, phones and bookkeeping: write the rule down first, then let the system apply it.
Thanks for adding to this,
Lee - Member since 2026 · 2 posts · 1 vote1d
Lee, I'm on the car dealership side, not rentals, but mine lines up with what Ezra said about automating the reminder. A reminder only helps if it lands with the person who actually has to do the thing. With our bankers' licenses the heads up came to me, not them, so all it really did was tell me when to start chasing. The date still got close every time because I'm not the one who renews it.
If I set it up again I'd write down who owns each date first, like you said, then send the reminder to that person early and to me a bit later as the backup. For landlords I'd guess that's the vendor's insurance or the tenant's renters policy, where the date is on someone else's paper but it's your problem when it lapses.
- Property Manager · Scottsdale, AZ · Member since 2016 · 84 posts · 16 votes1d
Lee, mine was vendor payments. I wanted an invoice to land in Jira, get approved, go out through Zelle, and close the ticket. My vendors already like Zelle. It’s fast and free. I couldn’t find a way to connect the approval to the payment that I was comfortable using, so I shelved it.
If I started over, I’d ask which part actually wastes my time. Sending a Zelle payment takes me a minute. Figuring out which property the invoice belongs to, whether the balance is still due, and whether I’ve already paid it can take a lot longer.
That’s what I’d automate first. Give me the invoice, the property, the amount due, and any prior payment on one screen. I’ll send the Zelle myself.
- 1dJames JonesPro MemberInvestor · Collierville, TN 38017 · Member since 2017 · 1k+ posts · 742 votes
Lee, you are right to write the process down first. At 236 doors, my in-house team at Memphis Passive handles leasing, maintenance, and collections, and I automate the tracking first: rent collection, reminders, and the vacancy and turn clock, so a house never sits empty because nobody noticed. What I do not automate is the judgment that costs real money when it is wrong: the rehab scope, the tenant conversation when rent is missed on day 1, and any call about money that is not routine. A system can tell me a house has been empty for 10 days. It cannot decide whether a tenant's story checks out, or whether a rehab line needs to move. I would automate the reminders and the tracking, and keep a person on the decisions.
- 1dMike FisherBusiness MemberNew Lenox, IL · Member since 2024 · 150 posts · 78 votes
The one I would not automate is the renewal conversation. A reminder that a lease ends in 90 days is a great thing to automate, a calendar flag or a task in your system. But the actual renewal outreach, whether it's a templated "your lease is up, here's the new rate" notice, tends to backfire. The good tenants read it as "we're raising your rent and didn't bother to call." A turnover costs vacant days, paint, cleaning, marketing and screening, so one phone call two or three months out ("anything you need fixed, and here's where I'm thinking on rent") usually keeps the tenant that already pays on time.
So I let software handle the timing and a person handle the conversation. Same split you described for screening and triage: automate the repeatable part, keep a human where a wrong move costs real money.
Mike Fisher, M Property Group LLC, managing rentals in Chicago's south and southwest suburbs since 1991.
M Property Group LLC | MF Cashflow Property Management4.997 Reviews - Member since 2026 · 89 posts · 31 votes1d
For us it was automated cleaning and turnover scheduling. We set the system to book a cleaner after every checkout, and it worked until a guest changed plans. A guest would extend a night or leave a day early, and the cleaner would still show up on the old schedule. More than once we had a cleaner at the door while a guest was still inside, and once a new guest arrived to a place that had not been cleaned yet.
What works now is a check before the job is sent. The system can suggest the turnover, but a person confirms the checkout date, the guest count, and any extra cleaning needed, and the cleaner confirms back. We also keep a backup cleaner for every property, because the plan that breaks is always the one with no backup. Automate the reminder, keep a person on the timing.
- Technology · Vancouver, BC · Member since 2026 · 261 posts · 67 votes16h
Hey @Alik Levin, @Daniel Jung, @Mike Fisher, @James Jones and @Jeanette Prestia,
Thank you all for coming back to this one. Every answer today added something new, and I've learned a lot from reading them.
Alik, I think you found the real time sink. Sending the payment only takes a minute, but working out which property an invoice belongs to and whether it's already been paid can eat a whole afternoon. Having the invoice, the property, the amount due and any earlier payment on one screen, with you still pressing send, sounds like the right split.
Daniel, a cleaner at the door while the guest is still inside is the kind of story that makes every host wince. Having a person confirm the checkout date and guest count before the job goes out, and keeping a backup cleaner for every property, is a smart way to protect the guest experience.
Mike, I really like your point about renewals. A phone call two or three months out to ask what needs fixing tells a good tenant they matter, and that's very hard to put into a template.
James, the line about a system telling you a house has been empty for 10 days, but not whether a tenant's story checks out, sums up this whole thread nicely. And Jeanette, it's great to hear the same lesson from the dealership side. Dates that sit on someone else's paper, like a vendor's insurance certificate, are something I think a lot of landlords only notice when it's too late.
If I were adding one thing for anyone reading, I'd start the way Alik described. Pick the one task where gathering the information takes longer than doing the work, let the system pull the pieces together into one place, and keep the decision with you.
Thanks for making this such a useful thread,
Lee - 14hJames JonesPro MemberInvestor · Collierville, TN 38017 · Member since 2017 · 1k+ posts · 742 votes
Thanks, Lee — glad that line landed, and I agree the decision stays with a person.
- Member since 2026 · 9 posts · 0 votes12h
Two that come up a lot with small landlords:
Automatic late fees. A fee that posts on day 6 based on when money settles will hit a tenant whose bank transfer went out on the 4th, or one who called ahead to say they'd pay on the 8th. Refunding it and smoothing things over costs more time than the fee was worth. What works better: base the fee on when the payment was started, not when it cleared, and keep a short note on the tenant's ledger for any agreed pay date so the automation skips that month.
Auto-dispatching maintenance. If nothing defines what counts as an emergency, the system treats a dripping faucet the same as no heat. The fix is a one-page triage list (no heat, active water leak, gas smell, lockout get handled now; everything else is scheduled in batches), a photo required with every request, and a person deciding before a vendor gets the work order.
I agree with your point, Lee: write the process down first, automate one step, and watch it for a month before adding the next.
Disclosure: I'm on the Tenantivo team. Our app handles rent collection with autopay and late-fee rules, maintenance requests with photos, leases and accounting on web, iOS and Android, so it's one option if you want to test this kind of setup.
- Technology · Vancouver, BC · Member since 2026 · 261 posts · 67 votes11h
Hi @Jason Stewart,
Thanks for adding these, and for being upfront about where you work. The late fee example is a really good one. Basing the fee on when the payment was started rather than when it cleared sounds like a small change, but I think it's the difference between a tenant who feels treated fairly and one who's on the phone asking for a refund.
Your triage list fits nicely with what James said about keeping a person on the decisions that cost real money. Defining no heat, an active leak, a gas smell and a lockout as the true emergencies, and asking for a photo with every request, gives whoever approves the work order what they need to make a quick, confident call.
Appreciate you sharing both.
Lee - Member since 2017 · 122 posts · 63 votes6h
Lee, we rent our houses by the bedroom, and that changes the answer a little, because five people share one kitchen, one front door and one trash day.
The thing I would not hand to a reminder or an app is any job the housemates share. A chore rotation for the kitchen and bathrooms sounds like the obvious thing to automate, and it turns into five people deciding it was somebody else's week. What works for us is a cleaner on a set day for the shared spaces, priced into the rent, so the only thing anyone has to remember is when clean is coming.
What automates well by the room is anything that belongs to one person. Each resident gets their own door code, made when their deposit is paid and ending on their last lease day, so nobody hands a key to a friend and nothing needs rekeying when one room turns over. Each one gets their own rent reminder a few days before the 1st. One person's late payment never touches the other four.
So my version of your rule: write down who owns each job first. If the answer is one person, automate it to that person. If the answer is "the house", pay someone and put it on the calendar.
- Technology · Vancouver, BC · Member since 2026 · 261 posts · 67 votes6h
Hey @Harrison C.,
Thank you for coming back with the by-the-room view. I think it changes the answer more than most people would expect, because a chore rotation looks fair on paper and then quietly turns into everyone's least favorite argument.
I really like the rule you landed on. If one person owns the job, the system can handle it for that person, and if the whole house owns it, you pay someone and put it on the calendar. Pricing the shared-space cleaner into the rent is a smart part of that, because nobody has to police anyone, and a new resident walks into a house that already works.
The door codes are a nice example of the same idea, too. When each code starts with the deposit and ends on the last lease day, one room can turn over without the other four residents even noticing.
All the best,
Lee
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