The process is a bit more complicated than that.

This is one of those complicated areas of the tax code.

Or would I be taking an unnecessary risk with this property that I’m already in such a good position on, considering current rates? 

@Jay Cho it's more complicated that you may think.You technically won't own the property!

Don't make it so complicated that you have to spend more time learning the software than it's actually saving you.

Plus it is less complicated to pull off. 

Finding an established group that finds a way to get deals done tends to be as helpful as anything as many of us have had experiences of weird and seemingly unnecessary denials.I do like to make sure that its a region they lend to and the type of project that they do.

(Instead of complicated private money or hard lenders)

Also, I have a month to month tenant in the SF, which could complicate the sale. - Conventional purchase with 20% down using a HELOC: Current cashflow from the SF could cover a big portion of the HELOC payment, but this starts to feel risky from a cashflow and funds available for rehab.- Conventional and move there/rent out my primary: Certainly the best option, but a hard no from my S.O.'

With the homeowner involved it gets a LOT more complicated on the legal, financial, emotional front and you’re dealing with someone whose mindset as to risk is a lot different than the professional investor.