The idea of having a cash flowing portfolio large enough to reduce or even fully step away from my regular work is obviously very attractive, but as a total beginner I don't want to set my sights too high without first gaining some experience in REI.

In addition to my role in mortgage underwriting, I also own a duplex, which has significantly fueled my interest in the real estate sector.

If I die, the property gets a stepped up basis and no taxes will ever be paid on the gains. 

Most correspondence lenders will not want you to in addition get a fee.

But my thoughts are will the hassle, time, money, spent on repairing give me any actual "gain" in the end?

Although I've gained some knowledge through reading books and online research, my experience in this area is limited.

Primary Residence, $0 capital gain tax per kid or spouse up to $250,000 each or $500,000 total. 

But a lot of these issues could have been avoided if I just had more experience.All, this to say, I want to continue investing in Real Estate but the pace I wish to do that cannot be directly proportional to the experience I gain.

In addition, Scottsdale has a limit of only 6 adults per house, no matter how large it is.These restrictions have nothing to do with red/blue states, they are the result of NIMBYs, who are all over.  

Third, note that any RE done in a traditional qualified account (SD-IRA, Solo 401K, etc) takes all that wonderful Cap Gain income and turns it into earned income.