If you sell your only overachiever to go with a more leveraged position, you could have 2-3 properties that may cover themselves or even provide a little profit, but when the rental markets shift (and they do), now you have 2-3 properties that all require you to supplement for their shortages. 

Regardless, guy did a great job so not going to complain about order of operations, but I am in a bit of pickle. 

Stable job for 20+ years.

Over this time I have acquired my contractor team and have vetted them through my job as a property manager, figured out my strategy(Off Market/Deep buying) and location.

Renting by the room (long-term) is stable but requires tenant management, while Airbnb (either by room or whole house) can bring higher revenue but needs more hands-on work—make sure to check Little Elm’s short-term rental rules.

While I may not have direct investing experience yet, real estate is in my blood, and I’ve spent years running numbers, learning the process, and preparing to make my first deal.Right now, I’m looking for: ✔ Smaller properties (4–8 units) that I can finance on my own✔ Larger properties (10–20+ units) that I am aware will require a more structured operational approach and strategic partnerships ✔ Opportunities near the University of Texas Rio Grande Valley (UTRGV) in Edinburg that align with my financial goals and my mission to support veteransBeyond investing, my long-term goal is to develop a transition housing program for student veterans—a place where veterans can live in a strong community while navigating college, career development, and civilian life.

Am I giving myself another job/business?

In some instances the estimate may be less important but rarely if ever do I not see a requirement for no appraisal unless the value is 4x the loan amount.

I understand this is not a requirement, but I have never received a damaged unit from an inherited tenant or any legal issues.

I can vouch for @Lane Berry he manages I think at least one our units in Houston, excellent job