Now you have 6 bedrooms in a 1400sqft home.

I wanted to get feedback on managing short term rentals in Hawaii. 

I own a SFH in Santa Barbara County (it's in an unincorporated area between SB and Goleta.)Ive had wonderful tenants since buying the property in late 2017 and have raised the rent just twice (still WELL under market value rent).

Once you have the property converted to two legal units, it's going to depend on business vs. personal useage. 

They are now in breach. 

@Sam Huang the title of your post says you are a wise and successful person.

I can refer a couple of great PM's in Orlando if you want to get another opinion or two. 

DM me if you would like to connect personally.

Mostly California but at least one east coast state in famous for it as well. 

on top of that if your talking remote rehab nothing is more risky in REAL Estate than a remote BRRRR