If you were you make $200/month in net cash flow, this is $2400/yr cash return on your $30k of equity, which is an 8% return (2.4k/30k), plus any tax benefits, appreciation, & principal paydown on the loan.

Need to go through it again but this is a potential option that may work.I'm thinking do a master lease with an option to purchase and 100% of the rents going toward the principal of the purchase or something similar.

We live below our means, and send extra to the principal to get it paid down quickly so we have more buying power.

Rentals conducted as “net leases” (the lessee is responsible for all lease expenses, including taxes, insurance, rent, operating expenses, any mortgage interest/principal payments, etc.), however, generally do not qualify as a trade or business.If Non-recourse:No debt discharge income results from a foreclosure or deed-in-lieu transaction involving only nonrecourse debt.

I note that you asked specifically about “cash-flows”, which has multiple components each treated differently for tax purposes.In general, you can start with NOI, next you have debt service and cap ex, which can get you to cash-flows.The interest portion of your debt service is tax deductible (possible subject to limitations) and the principal portion is not because you get basis in the asset for the loan principal, which generates a depreciation deduction.Similarly, cap ex is generally not deductible currently but the expenditure is capitalized and depreciated, similar to the initial basis in the asset.In summary, you have cash and non-cash tax items that cause your taxable income to differ from your cash-flows and taxable income * tax rate determines your tax liability.

If you can meet the numbers you have presented then you have a good chance of making it work.The PMI amount is in addition to PITI (Principal, Interest, Tax, Insurance) payment.  

If you do agree to a 10 year term, you will be gaining $630ish per month in principal reduction vs $345ish per month on the 15 year term. 

(Not sure why that matters)  The form stated:"Total amount to pay off contract in full" $____   We filled in the principal due."

All expenses including HELOC payments (principal + interest) will need to come out of the rental income on a month-to-month basis.I am aware of the recent Orlando ordinance allowing home sharing (http://www.orlandosentinel.com/news/orange/os-orla...), but will not be competing with them.Is this a good time to invest?

Could it be estimated as original borrowed amount + interest that would have been amortized or is it likely to be some nightmare # like  principal + interest + penalties + interest on penalties?