Here’s a quick checklist to cover your bases:Property Condition: Get a thorough inspection to assess major items like the roof, foundation, and HVAC—this helps you plan for any big repairs.Financials: Account for all costs, including taxes, insurance, maintenance, and property management fees if applicable.

He self-manages, is his own handyman and had to pull out the little equity he gained to pay for roofs and HVAC. 

Depending on the exact location, age, roof construction type, etc, there definitely could be a few things to watch out forAssuming the roof is of a reasonable age, it's still more than possible to cash flow with these properties, even after accounting for recent increases in insurance rates that we've seen.

If there is a leak, you may choose not fix it, but to plug.

Not currently leaking anywhere.  

The 2nd floor apartment is longer so the third floor can open out onto the roof of that 3rd floor (it's very solid - I've been up there and I'm 6/2, 250).

I used a business credit card to pay for a new roof and will use it going forward for all repairs and replacements of items. 

We have added new interior features and a new roof.

Roof is about 5 years old.

The comps in the area for MF's were at minimum 550k.Since purchasing the home there have been many updates to it to include a fully updated 2nd floor unit, updated bathrooms on both floors, new kitchen on the first floor, new roof, new driveway, new paver patio, updated front porch.