@Sankalp GoduguIf you are looking in the Columbus market I recommend areas like Hilltop, Linden, Eastmoor/ Whitehall, and Franklinton.

(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?

I own one rental house in Cypress, but with the current market I have not been able to find another existing single family home to buy that looks like a good investment. 

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. 

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.

I’d like to be able to validate observations, discuss data points, and talk about specific deals. 

Approach it like an investment.

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.

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