Again, fuzzy on the details, but they also have a mechanism set up for investors that have bigger pockets than 1500$.

All windows are in great condition, roof and mechanicals appear to be fairly new and in good condition.  

Yet, we leave our cars with mechanics every day.

Or a free oil change from your mechanic because he is the one you use for major work.I know we live in the freebie culture, but you use the word "relationship."

Better if new construction with exposed drywall, like most other mechanical and electrical systems.

For the purposes of this question, we need to know how things are organized.If the rental is held directly, or through a Disregarded Entity (DE), and the healthcare business is organized as a sole proprietorship or DE, mechanically, what you're proposing won't work. 

Depreciation is a lot better tax deferral mechanism than IRA and long term capital gain tax rates are lower than ordinary income rates applied to IRA withdrawals.

I can also not speak for the rest of the year, but during the summer I allow several days between booking so I can take to mechanic for lookover and adjustments. things can happen.

Things like construction companies, crane companies, field mechanic companies etc.

Mechanic, magician, mindreader.