@Corbin Dallas A strategy that a couple of old-timers that I was stationed with in the Air Force used was that they would buy a home with their VA home loan allowing them to get in with 0% down, and typically, regardless of branch, you’re at a duty station for at least 2 years.

Secondly do a IRS Section 1031 Tax Free Exchange so that you don't have to pay the tax. 

Area is mid/high end (Washington DC) and comps all have central Air.

I just pulled a random # out of the air. after reading the little help link.

This episode was aired back in June 2021, I believe.

Should I assume I can STR my property if I see air bnb homes currently listed around my area? 

The cost of installing an  expansion tank kit ( Expansion tank, auto fill with backflow preventer and air eliminator) is 1,100.

If not, kind of up in the air but I would at least offer to split it as you are both getting something out of the deal.  

Consider air sealing on the interior?

Is that central air that needs to be replaced, a new compressor?