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..?

I think that 25-30% is outrageous unless the company is doing an outstanding job increasing your occupancy rate compared to AirBnB, HomeAway/VRBO and other popular sites for properties in your area.

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.

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

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!

However, your best bet is to pick a medium-sized population city within those states with a lot of population growth.

This may be your best bet as it lets you hold off on formation, but its important to make the title company and the lender aware ahead of time so they can update title and prepare the loan docs with the correct entity name.