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.

Since I own my own company I get all of it except what I might choose to share with some of my employees.

The actual cost just to maintain the RE license in Texas is $1,000.00 minimum, which is including your Local Association Membership fee (mine is HAR and it costs me $439.00/yearly), MLS fee, Supra fees, Continue Education fees.

@Mike PolizziIf the 401(k) funds were used to improve the land already owned by your parents, this would result in a prohibited transaction because the land is already owned your parents.To learn about the prohibited transaction rules, see the following:https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-prohibited-transactions

Think of them as an employee in the sense that they would need to be carefully vetted, and would only receive payment on rent collected and not rent due for management of the property.

@Jacob May This is a common question for many clients I work with that are not employed as a "typical W2/salaried" employee.

@Antoine Martel@Alexander FeliceAntoine and Alexander,I am a W-2 employee is business development and in my job I travel to Las Vegas several times a year.

Is this an employee you anticipate hiring?