We want our kids to be able to be close to our families, so ideally, we visit Oahu a few months every year.I spoke with a few realtors and it seems like the best investment would be the condo hotel as they are legal Airbnb/STR.

Whereas, if you are holding $1,000 cash flowing property and the markets shift, you likely still have a cash flowing property that can sustain itself, and even help supplement another property that isn't in as great of an equity position. 

(I also don't understand how you have a hard money loan with a rate of 7.25%...)offering an equity position that you then buy out in just a few years seems like way too much complexity and risk when you say you just need 30K. 

Should I reach out to local agents, wholesaler like New Western?

Listing sites like Airbnb and Furnished Finder, and B2B relationships for referrals, insurance, and corporate bookings.

It sounds like you’ve got a solid foundation, especially with your experience in real estate private equity.Once you’ve isolated a market, building your team early is key.

I would be buying it most likely in my own name.

Or talked to owners of an existing one that looks like it is from the 90s to see if they would like to sell?

Approach it like an investment.

Check platforms like Zillow, Apartments.com, or Craigslist to view current listings and trends in pricing.