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. 

You can definitely benefit from having a retirement account that you are in total control.If you don't have any retirement accounts to rollover - then you will be limited to contributions of only $5,500 per year, so in this case you can probably have a conventional account (not self-directed) so that you can build enough funds before you self-direct.However, being a real estate agent makes you self-employed and therefore eligible for a self-directed Solo 401k, which is much more powerful then SD IRA.

It depends on how much eligibility you have remaining on your VA benefit.

Only way is to register an RRSP eligible fund with the securities commission which in turn invests in US properties.  

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.