In terms of cost, you just give up a percentage of the potential collected rents so there normally isn't' an up front cost to send someone to collections. 

Still, I'm concerned about potential tax complications given the property's location in Maui, my residence in California, and my in-laws living in Washington.Am I overlooking anything crucial here?

Since I was a medical student, I've always been passionate about making smart investments for my future, and real estate has piqued my interest for its potential to generate passive income and build long-term wealth.

This would be a non arms length prohibited transaction and would potentially result in the entire IRA being distributed is my understanding...the only way this could be possible is if the OP is or becomes retirement age in the next two years.

You can consider buying rental properties for steady income and potential appreciation, do house flipping for quick profits or explore REITs for a more hands-off approach.

I believe due to my citizenship, I could potentially get a hotel license (?)

-Researching Market Trends: Analyzing current market trends and identifying potential areas for investment.a.

The area seems it may be on the cheaper side of the close surrounding areas while at the same time holding the potential of having good cash flow.

Network with other professionals for insights and potential deals.

Doing a refi now would move me from a 4.5% interest rate to somewhere in the high 7% to 8% range, so I am thinking of potentially selling.