I work for a local house flipper in the Greensboro area (Winston Salem).

If you have $210,000, you can easily make 10% as a bridge/hard money lender in your local area.

But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

Do you live locally?

Locals know that and you can see that in DOM. 

You should find a lot of resources on BP but I think the most useful people to talk to would be MF builders and local officials in your target areas.

Go to BUILD YOUR TEAM at the top of the screen and look for local investors or meetups in your area.

One thing I’ve noticed is how many licensed agents don’t fully understand the contracts they’re using or the local real estate laws.

Ensure the sublease is explicitly permitted in a written agreement with your friend and aligns with local STR laws.

Local Houstonian here - Happy to connect.