@Jim Bo biggest mistakes investors make when doing business with friends is NOT treating it like a business arrangement.You'll need a detailed partnership agreement covering buyouts, capital calls and what happens if one of you dies.Why would you pay him while he learns property management?

I'm retiring in about 18 months and i would love to get into the STR business.

The whole appeal in REI was to maybe create a small business on the side with my spouse as a way to: eventually secure supplemental income, start building equity in RE and maybe creating a small business together in RE that would help us obtain financial freedom after hearing how risky things can be, I’m trying to learn: what are other RE investors doing to make money despite the risks around home repairs, vacancy, additional expenses (i.e property managers), etc.

I think the reality is that Airbnb is a larger company with a larger IT department so their software is more sophisticated and they have the staff to make software changes in a timely fashion to meet state and local laws.

I started a wholesale real estate business in November of 2020.

your deals his dollars has been around for decades.. as long as you pay him up front.. there are not thousands of investor just clamoring to do business with newer investors who have little training and no capital :)  if your in LA and if you have no already go to some of the FIBI meetings Jeremy Roll puts together they are the real deal. 

Should I be doing anything additional knowing he is running a business out of my house?  

I would say alternatively a personal business LOC but the origination charge of that alone could be 9%.

Well diversified business base, a university, access to good transportation, a strong workforce and affordable housing.All of those add up to a good long-term investment formula.Let me know if I may be of assistance.Paul. 

Regardless of that fact, I am well aware of my duty as a Real Estate Agent and the duty that I have to clients when entering that business relationship.