@Curtis Cutler Avoid cashing out your 401(k)/457 to minimize taxes and penalties, potentially up to 40%.

.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

Run your business as a business or risk it.  

I’d look into the cost of a 500 sq. ft. garage and compare it to the potential boost in sale price.

Hi Eli, This is a creative and potentially win-win strategy that could work well in the right situation.

This area was always a very high risk and should they rebuild?

But there's definitely risks that come with that as well.

The loss may potentially be disallowed.Best of luck

Angel investors might be interested, but you'll likely have to give up a portion of the ownership or future profits, and there could be potential complications in managing the investor's expectations and involvement.

A company that specializes might be a good idea, but if that isn't practical because the potential difference in taxes isn't that great it is something you can do on your own.