How much communication/involvement is there between a bank and a lender when a HELOC is associated with a property?

Not necessarily much help aside from unlocking doors in distant lands...Or, you will find an experienced investor agent who will be a wealth of knowledge and wise advice but isn't going to jump through hoops for no money (or even the "promise" of money later on) simply because he doesn't have to.Although I'm sure they do exist somewhere, it'll be very difficult to find an agent who will be all of the above.You will be better off in the long run associating yourself with multiple agents and using each one for their individual strengths based on each specific deal and location.

Their demands and threats do not bother me and I generally toy with them for a few months till they realise they are not going to win.

It also depends on the type of HOA and its associated expense.

I DO NOT know about costs associated with Airbnb and vacation rentals.

Based on the information you provided, the gross income from the property should be around $36,000 per year, and the property's taxes and insurance will cost a total of $11,400 per year.One thing to consider when evaluating the potential profitability of a property like this is the expenses associated with managing and maintaining the property.

By association, thank you for your service. 

Fast forward to tax time / refinance time, my accountant is telling me that the profit from Kingsbury, was actually a loss associated with quit claiming Mayflower back to the sellers.

“A primary concern was that the legality of purchase options associated with rent-to-own properties are largely untested and there is a possibility that these purchase options could subsequently be found to violate consumer protection and/or predatory lending laws,” KBRA said in its report.This presents multiple, serious problems for any investors who buy into a securitization backed by rent-to-own  or lease to own properties, KBRA said. 

After I pay all the bills associated with the house and the mortgage I am now at $2,990/mo.