@Keith Angell What are your long term goals?

@Jordan Meltzer congrats on the mid term biz and your success. 

However, I probably would not upgrade it but I would rent it out LONG TERM at least until you know your long term status in Portland.  

Then do a thorough research on tenant applicants (note: leaving this to a PM may be hazardous to your financial health) and choose the one that is most “stable” with the best potential for long term tenancy.This advice is contrary to maximization of rental income, but IMO will reduce expenses of tenant turnover, property damage, property management fees so much that the difference in bottom line income will be quite small.  

HELOC= short term useFixed (first or second) = long term use like a down payment.  

I would have asked you what your long-term goal is but you have already thought about it.

With countless loan options, complex terms, and strict lending criteria, it’s easy to feel overwhelmed.

For the couple hundred in extra 'cash flow' you get by doubling a payment's term, I'd much rather be done with it sooner. 

While short-term rentals in areas like Kissimmee, Florida, can pay for themselves and offer lifestyle benefits, the ROI typically doesn’t match what I see from my traditional portfolio of long-term rentals in North Texas.That said, short-term rentals can still be a great choice, especially if you're drawn to the area and the opportunity to combine personal use with investment income.

I am looking for suggestions on how to structure a partnership (short term) that will benefit him but allow me to be dissolve our partnership after a couple years as he isn't interested in long term holds.