Your Landlord Issues?

Question

Hey everyone — I’ve been doing a ton of research into how independent landlords manage their rentals (especially people with just a few properties), and I’m curious:

What’s the biggest pain point you deal with regularly?

Is it:
• Screening tenants?
• Lease paperwork?
• Maintenance coordination?
• Tracking payments and expenses?
• Dealing with legal stuff in your state?

I’m working on a tool that might help with some of this, but I don’t want to build something that misses the mark. If you’re a landlord with 1–10 units (or even more), I’d seriously love to hear:
• What tools (if any) you’re using now
• Where you feel the most friction or burnout

Thanks in advance!

if you’re open to a quick 10-minute chat so I can learn directly from you, feel free to DM me — would really appreciate it.

Brian Joseph OConnor · Answer

I'm a newbie with 1 property but renting out 4 rooms coliving strategy.  So I have 4 single occupancy tenants on 12 month leases.  I use TurboTenant for screening and collecting deposits/rent.  I use baselane bank for my business banking.  I self manage and it's far from passive but it's also not that hard.  You must have systems in place for automation, you must have good leases and leave nothing to chance.  I'm in the middle of my first eviction and it's not very fun.  I'm learning a lot and I'm sure I'll change some of my systems as I scale but I'm going to scale.

Corby Goade · Answer

I think the problem is that most self managers don't have a clue HOW their problems are arising- they think "that's just how landlording is," not knowing that they are creating their own problems through lack of process and professionalism.

Proper, legal screening and professional processes and documentation. Basically everything related to management.

Ryan Spath · Answer

@Alex Sanchez In my opinion the biggest pain point is when a person buys a property and does not treat this as a business. They have no systems & process to follow. Everything seems to be plugging along fine in this way of doing business until it is not.

The biggest tool private ll can use in my opinion is some type of online rent collection, I hear to many folks with a few properties that use venmo etc for payment. As I mentioned previously this works perfectly until it does not and you have to remove someone for non-payment, and then they venmo you 25% of the rent etc. and now you have to start over.

People often get a case of the tired ll syndrome when they do not have the proper tools/systems and do not treat this like a business even at the smallest level.

Matthew Becker · Answer

Kicking out a single more who has not paid rent for 3 months.  It really sucks.

There are a ton of apps out there what are you going to do different?

Ify (Bobby) Anizoba · Answer

Hey, I appreciate you bringing this up! I’m Ify (or you can call me Bobby), and I’ve been looking into solutions for independent landlords like us.

One tool I’ve come across that seems to address a lot of these pain points is Baselane. It’s designed specifically for landlords with a few properties and helps with:

• Tracking payments & expenses – Automated rent collection and financial tracking make bookkeeping much easier.

• Tenant screening & lease management – You can run background checks and organize lease agreements in one place.

• Banking for landlords – They even offer high-yield landlord banking, which is a nice bonus.

If you’re using any tools now, I’d love to hear what’s working for you and what still feels like a hassle!

Beth Reed · Answer

Maintenance coordination for sure.

anyone has suggestions on making it easier?

Caroline Baird · Answer

Hey! I love that you’re digging into this — I’m a small-time landlord and totally relate to the struggles you mentioned. I’ve been using Baselane for a while now, and it’s helped a ton. Rent tracking and expenses used to be the biggest headache for me. I had this messy system of spreadsheets, Venmo, and random notes, and it got overwhelming fast. With Baselane, tenants can pay online, and it automatically tracks everything and tags expenses by property. It’s made tax season way less painful.

Screening tenants was another thing I used to dread. Baselane has built-in screening through TransUnion, and I can keep all the leases and documents in one place, which has saved me a lot of back-and-forth and searching through old emails. Maintenance is still kind of manual, but I like that I can at least keep track of what’s been done and how much I’ve spent on each property.

Before this, I was piecing things together with Google Sheets and a lot of texting. Baselane just simplified everything. And honestly, the fact that it’s free (unless you pay for add-ons like screening) was a big plus for me.

If you’re building something for landlords with just a few properties, I’d say the biggest win is anything that makes life easier and more organized. Most of us are doing this on the side or managing properties in between a hundred other things, so the less friction, the better.

John Morgan · Answer

@Alex Sanchez

I self manage 29 SFR and it’s pretty easy. 10 of them are out of state. I do all my leases with apartments.com. I collect about half my rent with apartments.com too. It’s all free and easy to do online. I accept rent payments other ways too. I hire out all the work and have a few handymen. The most challenging thing would be dealing with people who are always late on rent. I used to let people get 3 or 4 weeks behind in rent. That doesn’t end well so I now start the eviction process much sooner. Once you give them a 3 day pay or quit notice, they seem to find the rent $. lol

Matthew Becker · Answer

I agree with John 20 or 30 is easy if you are organized and have systems.  50 gets to be more of a job.

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