I'm in the market for entity config and tax planning/prep.

I do intend to stay close to home - but home provides only annual opportunities and I’m looking for year round possibilities with tax deed properties. 

Winterizing Your Home: Tips for Draft-Proof Windows and Doors" – Offer seasonal advice."

I used to live in the city and the taxes and water bills are nightmares.

Quote from @Zara Massoud: Your new PM is correct and the old ones were wrong.The property manager must have your social security or tax ID number on file.

However, there is no specific holding period contained in the tax code or regulations and there is no "safe harbor." 

At a high LTV your leverage will be magnified.If your cash flow really is break even (I have my doubts) then with the magnification resulting from leverage, you could produce a fairly good return (ROI from leveraged appreciation, equity pay down, tax benefits).Good luck

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.

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.)

I've been knocking on doors, there is one that seems like it's abandoned, however despite finding the owners name from tax records I cannot seem to get in contract with them to make an offer (despite trying x, y and z).