She only did maintenance, but did replace the roof and AC condenser after the fires in 2016 (insurance paid).

I am not too worried about the basic lipstick rehabbing but I will definitely need to hire contractors for the more complicated repairs: plumbing, electric, roofing etc. 

We thankfully wouldn't be contracting out much but roofs and electrical.

FL has hands down the WORST cost's and process's for roof replacements I have every experienced.

Do you save three months of vacancy for each unit and $50,000 for the roof replacement?

Prop tax's some of the lowest the country very low insurance stucco houses tile roofs and desert landscaping all lead to ease of maintenance over time compared to FLA which of course has all sorts of weather related issues that is detrimental to houses .. high prop tax and sky high insurance ( certain areas) But its also growing.. so there is that.

What about leaking roofs or accidents you can't predict?

They ones that need new roofs, have broken pipes, no heat source, or have water damage.

I'd think it's odd for a contractor to ask you to cover their fees for licensing, they should just build that into their bid.Typically for smaller contractors doing windows and doors or re-roofs we've seen them add a permit fee which covers our services the cost of the permit and also most of the time puts money back in their pocket.

So she stepped into a fully functional office/ patient base and my purchase included all the equipment fixtures everything which of course gave me substantial accelerated tax bene's.. its a NN lease so I only am responsible for the roof and exterior ( roof  was 5 years old and with no hail in this area it will last long time).