Since you're focusing on affordable markets in the Midwest and South, it’s important to verify rental demand, property taxes, and local landlord laws.

Lower Property Taxes and a booming STR market.

My son currently lives in the townhouse b/c he is going to school and works in the area.Since he is young and starting out in life, I would like for him to only cover the basic costs (taxes, HOA, utilities) just enough for me to break even (I believe that will put him slightly little lower than market rent rates). 

The Annual Owner Statement should break down all the expenses that the owner's tax professional then figures out how to deduct and on what tax schedule.So that way the owner can expense everything throughout the year?   

How do you pay for the tax and insurance?

A common mistake in my area is to ignore Hotel Occupancy Tax.

The absolute best way to avoid taxes is not earn income.  

Thanks  I am not a CPA or tax expert.  

Bonus depreciation will finally be phased out in the 2027 tax year This is well said

The only taxes I remit directly now are the tiny town tax they implemented of 1%.I just take my net income spreadsheet and calculate the 1% and give them a check.