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 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). 

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.

Increase your earnings, reduce expenses, save up, and invest.

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

He is busy working at the hospital and doesn't want to deal with tenants, toilets, taxes, trash, and all that haha

So you are able to get the cash flow, tax deductions, etc.

Most Florida markets will share some dynamics though like taxes and insurance. 

Usually the numbers don't work to build in these neighborhoods, unless government tax credits, etc.Do you see the problem with your two statements:"The turnover costs could/will be high"and"How much more damage could they do?"