I'd look into the capital gains tax implications if you sell it now vs holding on to it.Yea, I've done the math on when I would have to sell by to qualify for a 121 exception.

I've been on this board since 2010 and haven't found an example yet.

There were some years ago when buyers would just take over the lease and that is it, the value stayed the same and it was transferred in escrow to the new buyer if they qualified. 

Listen to the advice you've received from many others, and let the HOA/Condo Board resolve the issue. 

I believe I can qualify for the HELOC on my own, saving my wife with additional debt ( when used) on her credit.Is there anything to think about if I apply to the HELOC solo?

He's someone that I met through the meetups and has a lending business called mr qualified https://mrqualified.com/.

This is how I qualify properties I am considering.Underwriting Made Easy for Short Term Rental Investors (biggerpockets.com)

Quote from @Brandon Croucier: I’d be looking to get into a DSCR loan.These loans are qualified by the properties income rather than your income, can close in an LLC, and also do not report on your credit report! 

One possible way is to qualify for a loan, get a house with multiple bedrooms, and rent it out to multiple people.

We did not have institutions coming on board previously.