We use it about 2 weeks...and from Nov- May it is not usable due to the fact it isn't insulated, or heated.Taxes were a whopping 14,000 this year, Am I correct in understanding that we can only deduct 47 days/ of 365?

For a business if you do not do 1099s don't plan on using the tax deduction.

As for writing off the cost (interest) of that money if you pull money out of House A to purchase House B, yes - that is an allowable deduction. 

The remaining interest can still be used as a tax deduction if you qualify (many people will just use the standard deduction).

That is good because I had just raised my deductibles on my insurance to $5,000 to save premiums.So that is the upside of being a blue collar landlord as I see it. 

Married couples get a tax break, but I wouldn't get married for another deduction!

I wouldn't put too much value in the deductible interest of using a HELOC to pay the 50k in credit card debt.

I only foreclose if I've xferred the deed in a sale;  lease option avoids that necessity, at least in theory, but some buyers are reluctant  to buy under option for various reasons, some being they worry or don't trust they'll get the deed at the end,miss out on some tax deductions if they're not owner, etc.Having a cancellation clause in a lease for the option in case of default sounds good, but by making reference to another contract in one contract,could be perceived as tying them together, negating any perceived initial benefit of having separate contracts.

If so your VA loan will be zero down and no PMI VA financing allows no "monthly MI," but the VAFF or VA funding fee is 2.15% for first use and up to 3.3% for second use is in essence still a form of MI being levied upon the borrower, just to clarify. 

Is the $550 net after deducting taxes, vacancies, capital exp, prop mgt (assuming you will do this), HOA, etc?