This place needs a roof and central air, but I'll know more after looking at it. 

Have you tried looking further into properties that have "distress signifiers" such as a shabby roof, uncut tall grass, etc?

My fee is based on unit count and accessibly along with other factors such as, do you want roof reports?

Roof, windows, flooring, etc? 

The Ant problem was not obvious until we ripped down the drywall from a small roof leak that we did see.

The home was originally built with four units but the city said there wasn't enough parking (so each 5bd unit basically has it's own connected 1bd mother-in-law apartment with kitchen and everything).Here are a list of my concerns: 1) Deferred maintenance  (a lot of vinyl flooring in bad condition, original roof may need to be replaced in the next 5 years, etc...).  2) Fewer units make vacancies, or a bad tenant causing damage very costly. 3) I don't have the cash for the down - I either need to find a partner or sell or refinance an existing property.To address some of these concerns: 1) I have a handyman I've used for years who could hammer these things out on a schedule that I could afford.  2) I've never had an issue keeping my unit occupied (I've even had the same tenants in one unit for over 6 years).  3) I've never partnered, but I'm willing to do so now if I can find the right person.Please share your advice!  

I always ask about roofs, water heaters and hvac here in FL to have an idea of the necessary repairs before I go see the property.

A gutter serves to divert the rain to one direction and keep water from traveling down the roof through cracks in the door frame, weatherstripping or siding.

Some rental owners have active maintenance programs and actually have reserves or means to replace worn out roofs, driveways, windows, hvac, plumbing, etc some not so much..Without going in to too much detail, does it look on first glance like they milked the property and are looking to pass all the deferred maintenance and major replacement costs on the next owner?

Common things I would look for is "Age" of the Roof, "Age" of the Hardware(Furnance/Hot Water/Etc) also if it has a basement which is an issue in the North and the tenant's History and Payment.