So if banks don't typically allow this transfer, how do people make it happen? 

I can print a "statement", but it's just going to say x amount of btc was transferred into this account, cool that tells you nothing more than what I've already given them.I know this comes down to them just not comprehending how bitcoin works, but how do I give them enough to make them happy?

You will have to monitor how much megabytes in data transfer that you use while uploading your videos to the cloud. 

We have acquired two note deals and are working through the pains of the infamous Peak bail out and getting our files transferred. 

In New York we have many code and compliance issues in every direction that can hold up the sale or transfer of title at closing.

Being a lawyer doesn't give you some magical purview of every legal field so I question their ability to discuss the legality of it in the first place.In regards to the tenants: If they've paid a deposit but haven't responded to your requests to transfer keys and pay first month's rent, then you haven't transferred possession of the property yet.

Coincidence, but is there any advantage to that bank being the my lender, would I get fees reduced or is there some easier less costly 'transfer' they can do since they already service that property?

The only exception is wire transfer, which is typically the only method accepted by title companies when bringing cash to closing due to the fact that it is not reversible.

When I bought a duplex last year, I came up with a letter notifying existing tenants that they have a new landlord and explaining that their security deposit was going to be transferred to me, how I wanted rent to be paid, and how maintenance requests should be handled.

Another option: Get a credit card with zero interest (and do a balance transfer).Find a company (RDC Capital, local bank/credit union (smaller bank)) that will give you line of credit (commercial) and pay back those loans with the LOC, which should be fixed after the "draw" period (20/30yr if possible). 3Hope this helps.