A legal duplex will have everything separate.  

I'm wondering if there's a software out there that could connect 2 separate VRBO accounts to resolve this issue.

Recently I bought a retail center and that deal has been making me think more about if it would be wise to set up a separate management company for all the properties. 

If you do place the property in her name, you've got a Gift Tax (Form 709) to complete. 

I’m on the deed, not the loan for the current house I live in here in GA. 

As a Canadian looking to invest in the states I’m wondering if there is any like minded Canadians in here who would be willing to chat! 

These structures are significantly more complicated than a typical 1031 Exchange structure and there are inherent risks involved in the transaction, some of which are discussed below.

Inherently the steps are the same as if you were purchasing with financing save potentially less closing costs and ability to close sooner (if needed).The terms of your offer (ie -contingencies, closing cost splits etc) will determine what is different. 

His girlfriend, in her early 20s, does not have SSN nor does she have an ITIN and she's unemployed so she cannot get screened.

However, I didn't lay out what that seller financing offer would look like because I'm really not sure if a deal can be made or how that financing would look.I'm hoping to find a way to get the home owner some money in her pocket if possible, although I need room for an investor to fix the issues and hopefully buy the lot back from the auto repair shop.