The answer to that question depends on your personal wants, needs, and goals for you and your loved ones.

You want to be the reference (in terms of knowledge)- Understand how to do the financial modeling of this type of asset or if you outsource, make sure that person is available when you pitch. 

I personally would be their agent, but I am very hesitant to partner with people unless I have fully vetted them.I would be their agent on a few deals, and then you would decide if you want to partner with them.

He would pay my mortgage payment and assume all responsibility for home maintenance until such time as he can qualify for financing. 

At that point you pivoted to AirBnB, and you say that is sometimes covering the mortgage.I personally don't see a reason to stay in the house.  

Both an IRA and 401k can leverage with a mortgage, so long as the mortgage is non-recourse - meaning no personal guarantee from you.  

Trash, miscellaneous such as water charge for a water leak, umbrella policy or other asset protection, book keeper/tax person, etc.  

We had personal savings and put down 5% with a conventional loan.

I personally only buy STR'S where I would want to go on vacation. 

Exactly as david said, putting the responsibility of replacing the furnace filter is a great way to enter the property and make sure that things are all OK.