So I can’t find a simple answer as it’s only one piece of puzzle- as supply and demand have huge impacts.Anyway, the good news is if you are really holding for 10-30 yrs, you don’t have to worry about this (too much). 

With all this in mind, I would have to second @Brendan Miller's recommendation of heavily considering selling as it doesn't sound like there's much cash flow to offer an attractive reason to hold.The only other piece of this puzzle is to determine what your goal is so that you can effectively leverage the gains.

Time and experience are also important pieces to the puzzle. 

The ideal first piece of the puzzle would be an agent who focuses on investors and has repeat OOS buyers.

Puzzled why so many would be available? 

Another piece of the puzzle is my wife and I just purchased our first home.

We think that the key to unlocking this house hacking puzzle is financing the project, without having to first sell our primary residence, or break the bank with monthly interest payments ... something like acquire, renovate/build, close.Thank you in advance for your patience and feedback on what is likely a very newb inquiry, and a situation that countless other boomers may be facing.Kind regards from NY,Steven P.Saratoga

I think wholesaling is a necessary piece of the puzzle, even though it needs more regulations.

This is such a unique business opportunity I don’t want to go to waste, but it’s puzzling to say the least.

Once you are ready (financially) to jump into an OOS market, the first piece of the puzzle is a real estate agent.