3 mistakes I made early as a small landlord in NYC
Investor · New York, NY · Member since 2025 · 92 posts · 71 votes
3 mistakes I made early as a small landlord in NYC
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Jonathan Taylor SmithBusiness Member
Rental Property Investor · Durham / Raleigh (Triangle), NC · Member since 2015 · 841 posts · 802 votes@Parris Taylor... Each valid concerns that can cause problems for new landlords. Have you made corrections? For example...
1. I set my mortgages to auto-pay 3 days before a late fee would hit, which tends to be after the 20th of the month; whereas my rents clear well before that (even those who pay late).
2. Tenants do not have my cell number. And I make sure those who obtain it somehow (usually my lapse) never get satisfaction from texting or calling me directly. All will get the same response of "Thanks for letting me know - but I need you to open a ticket on that in the portal." - But I would make an exception to that for FIRE.
3. If they cannot sign the lease digitally or otherwise make use of online tools, they'd better get a family member or friend to aid - otherwise they do not qualify to rent from me, as I'm leasing properties in 2025, not 1995.
I find that you get from tenants (and people in general) what you accept. I set my standards and tend to stick to them. Most people thereby get on my page. And those who won't would have just been problematic to my life anyway.
Blue Chariot Realty & Management4.915 Reviews
15 Replies
- 1yJonathan Taylor SmithBusiness MemberRental Property Investor · Durham / Raleigh (Triangle), NC · Member since 2015 · 841 posts · 802 votes
@Parris Taylor... Each valid concerns that can cause problems for new landlords. Have you made corrections? For example...
1. I set my mortgages to auto-pay 3 days before a late fee would hit, which tends to be after the 20th of the month; whereas my rents clear well before that (even those who pay late).
2. Tenants do not have my cell number. And I make sure those who obtain it somehow (usually my lapse) never get satisfaction from texting or calling me directly. All will get the same response of "Thanks for letting me know - but I need you to open a ticket on that in the portal." - But I would make an exception to that for FIRE.
3. If they cannot sign the lease digitally or otherwise make use of online tools, they'd better get a family member or friend to aid - otherwise they do not qualify to rent from me, as I'm leasing properties in 2025, not 1995.
I find that you get from tenants (and people in general) what you accept. I set my standards and tend to stick to them. Most people thereby get on my page. And those who won't would have just been problematic to my life anyway.
Blue Chariot Realty & Management4.915 Reviews - 1yWilliam J AndersonPro MemberPortsmouth, VA · Member since 2024 · 36 posts · 30 votes
Mr. Taylor,
I completely agree with your point about the drag on cash flow. Too often, tenants neither realize nor care about the impact their late payments have. I also agree with Mr. Taylor-Smith’s perspective—tenants should be held to the standards you set. Regardless of who they are, if the rent is late, the late fee applies. Conditioning tenants to follow your process is key to running the business smoothly.
For our part, we use RentRedi, which works well for most of our tenants once they understand it. When a tenant texts about maintenance, we respond by directing them back to the app—unless, of course, it’s an emergency.
Ninety days prior to lease expiration, we send tenants a formal notice. We also conduct a walkthrough, even for those renewing, and answer their questions at that time. If the new lease isn’t signed 45 days before expiration, we send a letter on company letterhead advising that if it isn’t executed by the 30-day mark, the lease option will be withdrawn and they’ll have 30 days to vacate. In practice, tenants usually comply well before reaching that point.
This process has encouraged tenants to turn on their RentRedi notifications and stay more engaged overall. Thank you for sharing your insights—it’s reassuring to know we’re not the only ones navigating these same challenges.
- Investor · New York, NY · Member since 2025 · 92 posts · 71 votes1y
@William J Anderson Appreciate you sharing this—sounds like you’ve built a really buttoned-up system. I’ve tried some of the “download the app, follow the process” tools too. My issue is that most of my tenants won’t touch them, and I end up back where I started: calls, texts, and late-night knocks.
For me, the real challenge has been: how do you get compliance without creating more tech friction for tenants who don’t want to log into anything? That’s been my headache to solve.
Curious if you’ve seen pushback from tenants who just won’t adopt RentRedi?
- 1yWilliam J AndersonPro MemberPortsmouth, VA · Member since 2024 · 36 posts · 30 votes
Quote from @Parris Taylor:
@William J Anderson Appreciate you sharing this—sounds like you’ve built a really buttoned-up system. I’ve tried some of the “download the app, follow the process” tools too. My issue is that most of my tenants won’t touch them, and I end up back where I started: calls, texts, and late-night knocks.
For me, the real challenge has been: how do you get compliance without creating more tech friction for tenants who don’t want to log into anything? That’s been my headache to solve.
Curious if you’ve seen pushback from tenants who just won’t adopt RentRedi?
Mr. Taylor,
We have seen push back however, we have stood firm on our assertion of the system and it is incorporated into our leases. As a final push we have had to let some tenants know that if they are not going to comply and utilize the app then they may want to consider being great elsewhere. When faced with this choice they have all complied. The market in our area is awesome for finding great new tenants at this time. The app allows us to track maintenance requests, track rent payments, track and digitally sign leases as well as complete the application process. All around it works for the tenants and us. I should add that we dont have anyone who is disabled or could not use the app however, if we did we would make an exception as well.
- Investor · New York, NY · Member since 2025 · 92 posts · 71 votes1y
@Jonathan Taylor Smith You’re spot on about setting standards—it really does set the tone early. I like your discipline on not letting tenants bypass the portal.
That said, in my experience (especially in NYC), a lot of tenants either won’t or can’t adapt to portals. Some don’t even have email set up on their phone. I get the philosophy of “if they can’t handle it, they don’t qualify,” but that screens out a big chunk of otherwise good renters.
For me, the bigger puzzle has been: how do you enforce structure without forcing tenants into tech they’ll never use? Still trying to find the sweet spot there.
Have you run into tenants who flat-out refuse the portal but are otherwise solid renters?
- 1yJonathan Taylor SmithBusiness MemberRental Property Investor · Durham / Raleigh (Triangle), NC · Member since 2015 · 841 posts · 802 votes
@Parris Taylor - I provide "affordable housing" to a wide variety of persons in different programs. Beyond just Section 8, one such program is for disabled persons, and includes stroke victims, elderly, etc... So YES - I will make certain accommodations for the reasonable capabilities and circumstances of the person. To do otherwise would be cruel. You can't tell a stroke victim to figure out how to use the portal. So I have a staff member who such persons can call (NOT ME) to handle things like opening a ticket in the portal. But it has to be reasonable for the condition and circumstances of the person. Is there a legitimate reason they can't use technology?
Blue Chariot Realty & Management4.915 Reviews- Investor · New York, NY · Member since 2025 · 92 posts · 71 votes1y
No legitimate reason at all. I think there are folks unfortunately who aren't good with software so they require added support (in my case, 20 mile drive to sign lease agreement in person).
The tough part with portals isn’t just the few tenants who can’t use them—it’s having to teach every tenant how to use it, while also learning the system yourself. By the time you’ve walked everyone through it, the “time saved” starts to disappear.
That’s why I’ve been trying to keep things simple: one channel tenants already know, and a backup plan for the handful who need extra help.Do you feel like your portal actually saves time overall, or do you still end up hand-holding?
- Investor · New York, NY · Member since 2025 · 92 posts · 71 votes1y
If the system’s built into the lease and framed as non-negotiable, most tenants will fall in line. The key seems to be making sure it actually makes their lives easier once they’re in it.
I'm trying to strip out as much friction as possible. Instead of forcing tenants to learn a dashboard, I’m trying to find tools that let them do everything in the same channel they already use—chat on mobile. Maintenance, rent, leases, applications—all handled in one thread, no logins, no extra steps.
End of the day, I think tenants push back less when the tech feels invisible.
Do you find the app you’re using smooths things out for tenants, or do you still have to spend time helping them through it?
- 1yWilliam J AndersonPro MemberPortsmouth, VA · Member since 2024 · 36 posts · 30 votes
Quote from @Parris Taylor:
If the system’s built into the lease and framed as non-negotiable, most tenants will fall in line. The key seems to be making sure it actually makes their lives easier once they’re in it.
I'm trying to strip out as much friction as possible. Instead of forcing tenants to learn a dashboard, I’m trying to find tools that let them do everything in the same channel they already use—chat on mobile. Maintenance, rent, leases, applications—all handled in one thread, no logins, no extra steps.
End of the day, I think tenants push back less when the tech feels invisible.
Do you find the app you’re using smooths things out for tenants, or do you still have to spend time helping them through it?
I do find that the app smoothes things out for tenant. However, I think more importantly the App has to work so we have to be on top of things when the tenant makes a complaint through the app as well. We have not had to help tenants through the app as most things are self explanitory.
- Investor · New York, NY · Member since 2025 · 92 posts · 71 votes1y
@William J Anderson Totally agree. The tech only helps if what happens after a tenant submits a request actually gets handled. Otherwise it just feels like their complaint went into a black hole.
In your experience, is the harder part jumping on issues quickly or making sure tenants know you are on top of it while it is being fixed?
- 1yWilliam J AndersonPro MemberPortsmouth, VA · Member since 2024 · 36 posts · 30 votesHonestly neither are a problem, I get an email and app push notification instantly when the tenant submits a maintenance issue. They are notified immediately as I go through the steps to mitigate it. Wether it is being reviewed, put out to bid, scheduled or in progress or completed. So the tenants are constantly updated. This is the part they really appreciate the results.
Quote from @Parris Taylor:
@William J Anderson Totally agree. The tech only helps if what happens after a tenant submits a request actually gets handled. Otherwise it just feels like their complaint went into a black hole.
In your experience, is the harder part jumping on issues quickly or making sure tenants know you are on top of it while it is being fixed?
- Investor · New York, NY · Member since 2025 · 92 posts · 71 votes1y
@William J Anderson Got it! Which step in your process took the most work to get right? The alerts to you, the status updates back to tenants, or lining up vendors so the updates are accurate?
- 1yWilliam J AndersonPro MemberPortsmouth, VA · Member since 2024 · 36 posts · 30 votes
Quote from @Parris Taylor:
@William J Anderson Got it! Which step in your process took the most work to get right? The alerts to you, the status updates back to tenants, or lining up vendors so the updates are accurate?
None of the parts you refer to were hard. The alerts are automatic in the app, the status updates are automatic in the app and we have a decent cadre of contractors to do the work that we cant or wont do. The hard part was getting those in our company to recognize that once there was an alert we have to communicate internally before communicating externally. but weve since straigtened that out and its no longer an issue.
Hi Parris! These are definitely relatable challenges for small and sometimes even corporate landlords. Thank you for sharing. There's some great tips in this thread already but wanted to chime in.
1. This is a tough one. I think a lot of landlords experience this problem. Definitely create a strict late fee policy if you don't already have one and use a software that can auto-apply the late fee and communicate late rent for you. That way you don't have to be the bad guy :)
2. Everyone hit on this point but definitely try to keep your personal information private. You can always use software or other alternative solutions for tenant communications and provide them with a list of numbers for emergencies. Once you set this boundary, tenants will respect it. Just make sure they know the best way to contact you.
3. Over 50% of tenants these days prefer everything to be online (applications, lease renewals, looking for rentals, rent payments, etc). It makes their life easier and helps them automate tasks like monthly rent payments. I definitely recommend setting tenants up using a good property management software. Lease renewals are easy and all they need to do is e-sign via an email or text. Most tenants (especially good tenants) will appreciate this.
I know I referenced tech solutions in this post a lot so feel free to DM for specific recommendations.
- 1yDrew SygitBusiness MemberProperty Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
@Parris Taylor where are you finding tenants that don't use email?
We deliberately got rid of signs and newspaper ads over a decade ago - to avoid these types of tenants.
All our ads are online, so you need internet access:
1) To find them
2) We only schedule showings online
3) To apply online
4) To submit applications docs online
5) Holding Agreements and Lease are only signed online
Funny story: took over management of a property with existing tenant. Tenant claimed they were an invalid and couldn't leave their home, so we had to pick up their rent. As we took over at beginning of month, we made a one-time exception to go pick up the rent. Guess what we picked up? A money order! FOund out the tenant's daughter went and got it. Told tenant if you can get a money order you can either mail the rent or deposit it directly to our bank. No problems after that. BTW: how was the tenant going to get us cash from their bank to pay the rent?
If you cater to tenants, they will take advantage of you.
Set boundaries, include payment options in your lease, include auto-renewal clause in your lease with a 5% rent increase.
Get creative!
Logical Property Management4.9460 Reviews
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