Most employees will never run a property like this as good as you will and I believe will require your presence.

@Buddy HolmesTo learn more about the IRA prohibited transaction rules, see the following. https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-prohibited-transactionsAlso, while an IRA can be invested in promissory notes secured by real estate, the note cannot be to you.

We just lost Discovery Communications, a fortune 500 company and what, 5 to 10,000 employees over night, and what effect has that had?

acquisition manager or field agent what have you.. all the bigger builders in our area have a w 2 employee that does just that.. its a great incubator.. and I mean great. you learn how to do development deals and that is where some big money is.I paid a 125k assignment fee to someone last Aug. who brought me a 92 lot development.. the guy could not have done this by just being a wholesaler he had to know enough about the industry to write the correct contract plus he put up the first 50k of his own money to get into contract its a 7 million purchase..

If you are paid a salary as an employee with no overtime, your income calculations will be more straightforward. 

There are a couple property management companies out there, but every local I know of manages themselves until they can hire employees. 

Wondering if this makes him my employee though?

The advantage to the medium-term rental is that you are probably not going to encounter laws/HOA rules that limit them (HOA can be tricky, so double check), they are less work than an STR, the money is still better than a traditional rental and the demand is relatively high if you are close to a college or a hospital or something with appeal that needs employees. 

I'm not to familiar with the mortgage pre-qualification of 1099 employees. 

If you want doors opened you first approach employers and find out first hand how they value a Masters and whether it is what they are looking for in future employees.