Managing tenants is no easy task, it takes such a wide skill set. 

Basically I would upload and organize my photos in RentRedi and I would publish and the lead photo would be like of the driveway or laundry area.

I'm sure I have a long road ahead of me but we all have to start somewhere.So basically, I want to get more info on section 8 housing.. whether that's flipping a building and then renting it out, or just purchasing an existing building, and renting it out.

It will familiarize you with the basic terminology and benefits.

It is free to post it if you use your cellphone camera.https://lapentor.com also has a free use for basic.

Basically, if your first home was purchased for $194K, you probably have VA eligibility for up to another $600kish home. 

Now, bank branches are staffed with lower-level trained monkeys that can't answer basic questions.

You could have picked it up, flipped it right back on the market for $300K without lifting a finger, or done a basic builder-grade renovation and sold it for $625K+.Also, most homes in the South End fall under RMF or R6 multifamily zoning.

It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).  

He is interested in REI, has good basic knowledge on REI and has more than enough saved up for down but hesitate because of current market, interest rate, rental demand, capex, first investment jitters, draw of stock market, etc, etc.