And for these newer companies I have to guess they simply have not encountered or planned on failing projects so its all new to them on where what why and how to deal with it. 

More chance of fraud ( There is always a new lender popping up with some crazy program and people fall for it and end up paying upfront fees, never to hear back from the lender) 3.

Start sending your sesume to all the big commercial PMCs in your area.You could also try residential PMCs, but they typically pay less.

I try to have a plan A, B, and C in place with tight acceptance and contingency periods. 

If you are able to make cash flow on the investment and have it pay for itself in the time of owning it, then it may make sense.

The new property can be purchased with the HELOC, but when doing your underwriting, the new property needs to be able to pay its own mortgage and the HELOC back.

Some platforms, like Airbnb or VRBO, may handle the collection and remittance for you, but it's important to verify this.Make sure to register with the Florida Department of Revenue and Pinellas County to file and pay these taxes.

They are good paying renters.

Was she paying rent to family during those years?

Is there any legal obligation to pay the unpaid utilities?