I could care less for your "sympathy."

Additionally, we had a wiring issue where power was cut to one side of the condo which I feel may be the from the rodents chewing.In total, I have had my maintenance contractor in there twice to make sure all openings are sealed in addition to fixing the wiring.  

Which equates to heirship issues, leins from the city for keeping the grass cut, interest in those leins depending on how old they are, and a host of other potential hiccups. 

However, the Tax Cuts and Jobs Act eliminated this restriction starting in 2018.

I would say if dems take house and senate and negate the trump tax cuts that will have a very large negative impact on small businesses who are a big driver In the economy.No matter what, 2020ish timeframe expect a decline in home values and economy

I have no information on your area and what rents go for, but I would be careful on being overly optimistic on rent, make sure to back up your numbers with research on Zillow, craigslist, rentometer, etc.

Just be careful and read up on using these machines before you use it.

We have been taking care of vacation rentals for other property managers for 7 years.

Most tenants do not appreciate kindness or reciprocate by caring for your property.

Your questions are good and appropriate— you will have state and federal forms to take care of.