I figure I'll get losses of 20-30% of the purchase price as a general rule.

Hey @Nelisa Lee, @Gregory Schwartz is referring to the profit & loss within QBO not showing the cash flow of each property since it does not factor in things like principal paydown, PITI escrow payments, CapEx, etc (those are balance sheet accounts). 

We don't know what states the properties reside.Florida, Georgia, Hawaii, Illinois, Indiana, Montana, South Dakota, Virginia have different laws.Oh, and by the way, an attestation to the insurer and others (mortgagee) will not change premiums nor constitute a “sale.”There are considerations such as the loss of asset protection after judgment (beneficial interest is personal property, not real property), but if the property is clear of a mortgage and the concern is title theft (a concern you raised), then putting the property into a land trust is probably a lower cost alternative to maintaining a debt (which irritates the wife). 

Jumping into any investment without knowledge can be a recipe for disaster or great losses.

If it will cost you considerably more in the future and loss of appreciation, lose of tax writeoffs and lose of cash flow in the meanwhile, than the amount of debt you are paying off, how does that put you ahead? 

Proper loss of rent.

My vision was this summer to rehab the home as a primary residence but now needing some creative ideas of what to do once we do a tear down.

My PUP still covers me on losses beyond that amount up to my insured level, which is another 2 mil. 

Hey Sartaj,Congrats for the success so far and for having a clear vision for where you want to go.

Not wanting to sell for a loss, we haven both rented out but are well short of being able to cash flow.