However, the vacancy is really low in my area and prices are really high so it’s a gamble most house hackers take.

In this scenario the property as a residential property is normally a terrible deal because they are basically selling it as commercial land so you might want to look into that.

I normally invite locals to the meetups.

Likely to be a silly question - do we put the offer for land on the same RPA as a normal property sale?

some maintenance is normal...and i'm skeptical of a contractor coming in and blanket saying "it needs a ground up reno"... could help more with pics...

You will convert from normal income (rental) to interest income which is taxed differently. 

Thanks  they would expect a furnished property and if you arent already a STR and just a normal LTR, that can cost a lot.

They had to get approval to do it though since it was outside of their normal guidelines.

Normally in a spot like this, we would recommend to a client that you sell your primary residence and claim your capital gains exemption under Section 121, but you have two strikes against you: (1) you have not lived in this property long enough to qualify for that, and (2) I'm hoping you already claimed an exemption on the sale of your other primary residence a few months ago, and you can't claim Section 121 exemptions within 2 years of each other. 

If you do that, they can adjust your escrows back to normal.