I recommend you look for a quality property manager to handle things for you. 

My plan is to also rent the main house so I don't have very clear how to handle it.

Each county handles this process internally - you'll have to reach out to your county.

Not everyone can put down 20% to start in the STR world and these are options to find an entry if someone desires.  

I am curious about how that is actually handled by other tax pros in real life scenarios. 

The city still has relatively affordable entry points, with most of the deals I'm doing falling in the $80k-$90k range and bringing in $1,200-$1,300 per month in rent.

That being said, it is a great neighborhood and good entry point for those wanting to get a little "discount" off the "standard" home prices in the Woodlands with great Conroe schools.

You can add Schedule C or Schedule E to your personal form 1040 return to handle taxable income. 

So, the first question they usually ask a PMC is about fees - instead of asking about services and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?

Presumably they have had rent increases, so how have those been handled.