He told me the nails holding it was loose, so he went throughout the house, re-nailed all the gutters.

As such, I would suggest being very conservative with your cash as loosing principle will be quite impactful.I understand your desire to earn the highest return possible, but keep in mind that you often need to take on higher risk to get a greater return. 

Lots of schedule Es I can not read or understand.I obviously know my rent "income" and my costs (especially since I make NO positive cash flow money on it and mostly loose money (last year I lost "only" -$1175) so i want to know what i made in appreciation versus how much I lost per year for the past 20 years. 

I feel the main reason the bank pays back taxes is to protect themselves of a tax foreclosure happening and they loose their security for the loan. 

The only other thing is the siding, roof and and any absent or loose flashing. 

Pieces of the roof are already loose and blowing in the wind again :/ 

I am considering keeping my current personally owned home/farm and renting it as horse owner property. already completely set for 2-4 horses. my personal interest rate on the property is 2.6% and I don't want to loose it.

If you locked in a better interest rate when you bought the house then you might end up loosing it  and replacing it with the current higher interest which could cut into your cashflow. 

We have been in the Smokies a long time, and many guest accidents, some of them life threatening over the years, could have been avoided with an annual risk management walk-thru:- Loose or rotting steps- Nails poking up through deck boards- Stinging insect hives or infestations- Ceiling fans that are barely hanging on- Loose deck, stair, and landing railings- And oh, about a hundred other things!

If something this simple and NON-panic is panicking you to loose sleep, your int he wrong business bud.