I would like to develop a model where I can purchase properties out of state and build up enough of a portfolio that it provides $5000-6000/month in income. 

Tesla recently purchased an additional 381 acres adjacent to the existing 2,100 acre site in SE Austin and is fast tracking the development to open next yearCompletion possible as soon as May 1, 2021, according to public documentshttps://www.bizjournals.com/au...

Can discuss the long term benefits of owning timber land  along with smaller development infill type projects that we do.. 

developing cities?

All it takes is one estimate to be off and a relationship issue develops. 

I found out later that buyer was doing a double close, rather than assigning, since he assured me he 'was developing it himself'.

If he has been doing it his way for almost 50 years there is a good chance he isn’t going to was to hear it frankly.That said, if you play along, even if you can’t use subtle techniques to move things along, you may win his trust and be given some buildings to manage- after which you can slowly change things.Above all else enjoy your time with him.

I work in financial management for the Air Force but really want to switch to CRE (commercial real estate) as I have developed a strong passion for real estate.

While I would be cautious here given how things developed, I would think that if you have done all of the relevant background research on the original applicant and he met your criteria (3x the rent plus the stuff I mentioned above - you'll need standards so you can treat everybody the same) then it wouldn't matter if he added someone else as his income and credibility should sufficiently cover.

I personally aspire to develop rhythms of a hybrid nature that allow for both and grow to accommodate pattern recognition wherein the approach is relevant to the target.