I’m over here on Big Island, up in the Kohala coast, and it offers some resort areas too on the sunny western side similar to Ko Olina on Oahu.So things to consider are:- Which Island- Your budget- Will you be financing or paying cash?  

Eliminate debt, establish a budget, and save.

I would look for a 5 bedroom if it is within your budget.

It's been so bad here, that I bought an STR in Indiana with another business partner in 2024 because there are minimal opportunities here - unless you have the ability and budget to extensively source off market properties here.  

My regret is not buying one in Hawaii or somewhere else where my family could spend some vacation time.

Could be the best money you spend on the deal!

Having a 15%-20% contingency in your rehab budget can be a god send!

We don’t use the 70% rule for anything except to decide if we’re going to look at the deal… and even then we just want to see if it’s close before we spend time running numbers.

But in my experience, you would be better off spending that same amount of time/hustle working a second part-time job with guaranteed income, then investing in buy-and-hold properties. 

I know it's over your budget, but is this the kind of property that would interest you: https://www.realtor.com/realestateandhomes-detail/194-Joliet...?