Small Landlords – What Are Your Top 3 Pain Points Managing Properties?

Question

Hey BP fam,

I’ve been self-managing a couple small multifamily properties (1-4 units) for a few years now and was curious to hear from others in a similar boat.

If you’re a small landlord — especially if you’re doing everything yourself and don’t use property management software — what are the 2 or 3 things that drive you nuts, take up too much time, or just feel like constant friction?

For me, it’s:

• Chasing tenants for lease renewals (always later than I want).
• Remembering what’s been done on maintenance and what’s still pending.
• Trying to keep track of everything without it turning into a spreadsheet from hell.

Chasing tenants for lease renewals (always later than I want).

Remembering what’s been done on maintenance and what’s still pending.

Trying to keep track of everything without it turning into a spreadsheet from hell.

Curious what headaches others are dealing with — always looking for better ways to stay sane and learn from others managing on their own.

Let’s hear it.

Kyle Wheeler · Answer

Landlord & Property Manager | St. Petersburg, FL

Great thread, Parris. Been there.

I self-managed my own rentals for a while before starting to help others manage theirs too. Definitely agree with you—chasing lease renewals and tracking maintenance gets messy fast without a system.

Here are my top 3 pain points:

• Late or inconsistent rent payments – Especially when tenants pay by check or want to pay in non-digital ways. It creates delays, excuses, and manual follow-up every month.
• Coordinating maintenance with vendors and tenants – I’ve had more back-and-forth text threads than I can count trying to coordinate schedules, get approvals, or find someone reliable on short notice.
• Tenant communication overload – Especially when tenants text you at all hours for non-emergencies. Boundaries can get blurry if you’re not careful.

Late or inconsistent rent payments – Especially when tenants pay by check or want to pay in non-digital ways. It creates delays, excuses, and manual follow-up every month.

Coordinating maintenance with vendors and tenants – I’ve had more back-and-forth text threads than I can count trying to coordinate schedules, get approvals, or find someone reliable on short notice.

Tenant communication overload – Especially when tenants text you at all hours for non-emergencies. Boundaries can get blurry if you’re not careful.

The best thing I did early on was set up repeatable systems—even basic ones—and slowly move things toward digital tools (like e-payments, lease reminders, and shared maintenance logs).

You’re not alone—this phase can be a grind, but streamlining even one thing makes a difference.

Rene G. · Answer

I had to figure this all out while deployed to Iraq. I built a bunch of handsoff systems and tested, trial and error until I dialed in everything into SOPs (took me about 10 years to get here though).

I call it "self-service" property management. I have automated newsletters where I give tenants seasonal email reminders with short how-to videos, I carry home warranties, everything is online eforms: lease/addenda e-signatures, condition reports inspections where tenants upload pictures and they automatically get save to the cloud, pre-leasing app so I don't have no-shows, I even have SOPs where I hire out my showings and it explains everything they have to do step by step, etc.

This took a lot of effort up front but saves me so much time now! I did all this because I committed to landlording forever and I want a rental biz that I control that practically runs itself. I call that cashflow forever and real freedom!

4Δ 𝓡𝓮𝓷𝓮 💪The Forever Landlord

Peter Tverdov · Answer

Most small time landlords spend to much time DIY repairs and value their time at zero. They are not organized enough to have lease renewals done, so rents do not get increased, tenants become MTM. The last one is having a bleeding heart and creating a back rent situation.

Those are the top 3 most common issues we see when our property management company steps in to service a home.

Paul Belessis · Answer

I fully self manage my 2 properties:

- (1) long term rental in Pennsylvania

- (1) short term Airbnb of my primary residence in Denver, CO

one of my biggest issues was the learning curve for the financial management part of the real estate. I wanted to keep the expenses separate from my personal income (kinda of like an extra savings account) while also setting myself up for an easier tax season and I also wanted high-yield savings too. I did a lot of research and finally came across Baselane and I LOVE IT. Soooo much easier to manage both of my properties (I keep them separate both income and expenses) in the platform, I can track cash flow, make purchases via the debit card, and export easy reports for tax season. It's the best decision I've ever made. https://www.baselane.com

Mohammed Rahman · Answer

Hey, totally feel you on this. I’m in the same boat — small multifamily, self-managed, no fancy software. Top 3 things that drive me up a wall:

Coordinating repairs — whether it’s scheduling with contractors, tenants not being home, or things dragging out longer than promised. It turns into a full-time job fast.

Rent reminders — even with good tenants, I still end up sending the awkward "Hey just checking in…" texts more than I’d like.

Paper trail chaos — lease docs, receipts, inspection notes… I’ve got stuff in my email, Google Drive, phone photos, hard copies. It’s a mess and never where I need it when I need it.

Jules Aton · Answer

Despite maintaining my properties the biggest headache has always been the inevitable leak, HVAC failure or toilet emergency which inevitably occurs at midnight on a holiday.

Colleen F. · Answer

@Parris Taylor I started to think about this a different way sometimes it isn't the task it is a general theme across tasks. 1. Timing (repairs, inspections, vacancies can be inconveniently timed). 2. Vendors availability/response (going out of business (retiring), callback. 3. Prioritizing capitol projects. What do you put on the list first. 4. The single tenant issue that I wish I could never hear again is a noise complaint. It periodically raises its head and causes problems. It is never big noise that you would evict for, it is that between tenant complaint is a small multifamily that you try to make people aware of but they forget.

My solutions 1. find a backup, do proactive maintenance and make the tenants aware you are human and what is an emergency, make leases end mostly in spring/summer. 2. have multiple vendors, be persistent, pay promptly, and treat vendors nice. I also learned to call the right vendor, make sure to look at some jobs and know a one man shop can't handle them and others and know that one man shop is your best choice. 4. mostly I tell tenants to work noise out between them although I have talked to some.

Peter Mckernan · Answer

For me it's the small things that are not repairs more like an easy fix by a tenant and not knowing what to do in the situation. Making sure the tenants coordinate being at home for the handyman/contractor when they are showing up (happens more often than not the tenant thought they didn't need to be there for access lol). The last thing for me yes getting people to sign the leases when they are suppose to sign them to get the rent bumped up.

The things that help on the list you gave. PM software, the software will put a checklist for what has been done and what has not been done by the handyman etc. There are plenty of softwares that remind you and the tenant that the lease is coming up for expiration.

Alecia Loveless · Answer

@Parris TaylorMy biggest headaches are finding contractors who have availability, finding qualified and quality professionals to help with the management of things(lawyers, accountants, bookkeepers, etc), being the primary source of contact for my tenants(I have a few that contact me multiple times a week over insignificant issues).

Small Landlords – What Are Your Top 3 Pain Points Managing Properties?

Small Landlords – What Are Your Top 3 Pain Points Managing Properties?

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