Scaling maintenance as a small landlord

[Frank D'Alessandro]

I'm scaling from 3-4 properties and the maintenance side is the part that's starting to feel messy. I rent out by the room for various reasons (house hack, high interest rates, wanting to have a second garage, higher cashflow)

While i'm at work, Tenant requests come through texts,or calls. Contractors/workers send before/after photos that get buried in message threads. I find myself screenshotting things, creating folders, spreadsheets and still losing track of what was actually done and when. When I need to reference something later (for a tenant, for taxes, or for the next job), I'm digging through old texts and photos that aren't organized with the actual work order.

I know at 3-4 (or even 8-10) properties a lot of people make spreadsheets + Google Drive folders per property work just fine. That's what I've been doing too. But for me the real friction is organization — photos getting lost and losing the history when I need to reference something later.

Curious what other small-to-medium landlords are actually doing:

• Are you still on spreadsheets + shared Drive folders, or have you found a lighter system that keeps photos and status tied to the actual job?

• How do you handle before/after pics and status updates from contractors without everything getting scattered?

• Anyone using something that gives you "one place where photos actually live" instead of scattered across texts (without jumping into a full bloated property management platform)?

Would love to hear what's working for other baby landlords in the same spot... any simple processes or tools that reduce the phone usage and digging around later.

Cheers!

[Mike Kirby]

Quote from @Frank D'Alessandro:

I'm scaling from 3-4 properties and the maintenance side is the part that's starting to feel messy. I rent out by the room for various reasons (house hack, high interest rates, wanting to have a second garage, higher cashflow)

While i'm at work, Tenant requests come through texts,or calls. Contractors/workers send before/after photos that get buried in message threads. I find myself screenshotting things, creating folders, spreadsheets and still losing track of what was actually done and when. When I need to reference something later (for a tenant, for taxes, or for the next job), I'm digging through old texts and photos that aren't organized with the actual work order.

I know at 3-4 (or even 8-10) properties a lot of people make spreadsheets + Google Drive folders per property work just fine. That's what I've been doing too. But for me the real friction is organization — photos getting lost and losing the history when I need to reference something later.

Curious what other small-to-medium landlords are actually doing:

• Are you still on spreadsheets + shared Drive folders, or have you found a lighter system that keeps photos and status tied to the actual job?

• How do you handle before/after pics and status updates from contractors without everything getting scattered?

• Anyone using something that gives you "one place where photos actually live" instead of scattered across texts (without jumping into a full bloated property management platform)?

Would love to hear what's working for other baby landlords in the same spot... any simple processes or tools that reduce the phone usage and digging around later.

Cheers!

We have 18 rental properties and have been renting houses for over 25 years. I don't have a single photo of a maintenance issue. Not one.

Sure, we have gotten a picture from a tenant saying "hey, we have a problem" but I've never kept one for my records. Never needed one later either. Keep it simple.....

I have one spreadsheet with 18 lines on it with addresses. Then 24 columns with the month and Cost for the 12 months. That's it. Simply fill it out during the year and everything is right there on one page for the CPA on Jan 1st.  Keep it simple.....