Use umbrella insurance as an additional safeguard, especially if you opt not to form an LLC.Avoid S-Corp taxation for rentals, as rental income is passive and not subject to self-employment tax. S

Who covers the tax bill when they don't pay the tax bill or the insurance? 

I make around $110k+ per year, live off around $75K, have a mortgage ($1900/mo for rent, escrow, tax), around $40K in equity, and no other debt. 

One thing to take into consideration would be the overhead costs of being a cross-border investor, such as entity setup, property management, higher lending rates and tax filing should you choose to have a CPA.

Honest... not great but we had other tax reasons to get into them.   

Is it fair that the county can raise property taxes due to a strong market?

Since part of your property is a rental, I believe a portion of your mortgage interest should be a tax deduction unlike your other debt.

I know how to use the basic features of QBO, as I do my own expense tracking, but my Bookkeeper is needed for the more complex entries (Loans, capital balances, reconciliation, data entry from PM monthly statements.)I spend almost 8k per year in QBO and Bookkeeping costs (Not including my accountant or tax prep.)

From a tax standpoint, there are additional disclosures to make when selling a business asset for less than fair market value to a related third party. 

I recommend that you find a trusted or recommended Mortgage Loan Originator (MLO), who can give you options for property-based loans (mostly investment loans) and they don't use your taxes but the P&L of the property.