Something like EaDo, midtown, maybe a small fixer around the heights (more heights adjacent than heights proper due to the budget) that is not betting on the neighborhood turning make the investment work.

Your best bet would be to call an insurance agent and ask for a quote.

You're just a bad bet, and the longer you stay, the more pervasive your stench will be in the unit.

I think it's fine to risk a small portion of your net worth on a gamble, but everything else means betting the farm.Speaking of farm, here are 50 acres in Hilsboro for $3M https://www.zillow.com/homedetails/NW-West-Union-Rd-Hillsbor...Dang, maybe if I..?

Your best bet here is to flip it or do some kind of rent credit program. 

You know, I'd probably bet you're right, but no need to be a d*ck about it 

Echoing Dave, your best bet is to approach people off-market; many owners of such land might not realize what they have.

Your best bet if you want to go there a lot is to either find one you can fractionalize with friends or find one just a little farther out, with less regulations, to buy and then short-term yourself.

So i would say your best bet is discover and make sure it graduates!

You could bet on less established destinations but it's much more speculative.