I'll use these next 20+ years to not only evaluate Real Estate, but other income sources (businesses) to see if I can find something.

Just tap into what talents you do have and offer that in exchange for shadowing and learning about the business. 

Is the mid term rental business that you have a 'rental arbitrage' business?

Part of the reason why the rehab was cost effective was because I have a long relationship with contractors, have experience, and I also give this contractor a lot of business.

I am actively expanding my STR consulting business!

Because I'm busy doing it, lol. 

Love AI in the business though. 

I am currently a student at Florida International University, studying International Business.

Most tools give you a glimpse of past performance.

Many people choose NOT to have this, because the administrator will then vet every investment you make to ensure you do not invalidate your IRA.Invalidating your IRA means that you've done a prohibited transaction and the entire account is then deemed as distributed to you.If you don't want checkbook control, then I recommend a plan administrator such as Equity Trust - www.trustetc.comIf you are sure that you're aware of all the rules around prohibited transactions and disqualified people (who you can and can't do business with), then a plan administrator like Sense Financial would be a good place to start talking.