Nothing wrong with the model, but I'd prefer not to give away most of the equity to the TK company. 

@Erin Schenk I am an investor and real estate agent in Bakersfield and have considered out of state as well, but for me, I prefer Bakersfield becuase I manage my properties myself which increases my cash flow and cuts down on vacancies and repair costs. 

Since you were willing to deal with an ugly driveway, my sense is that you prefer not to take on anything super costly.

I am also open to flipping if the deal is right but prefer to hold the property as my priority.For my current paycheck, I am in Senior Management at New Era Cap as a Program Manager of digital programs.

First, tell you boss at your company and make sure it's okay -- it doesn't do any good to make an investor mentor if you also lose your 9-to-5.As for approaching the individual: 1) explain why you're interested; 2) say that you did get the ok from your company, and that you're doing it in a totally private not-related-to-your-company way; and 3) offer to help out with his properties like you said.A key thing to be clear about -- if you offer to do any of your professional day-job work for him on the side as a favor for him helping you out, you need to be sure that your company doesn't mind you doing it.

Personally, I prefer properties with minimal cosmetic issues.

I personally prefer the stability of A Longer Term lease.  

There are lenders that will lend to individuals

You can join real estate networking groups in your city and attend some local events to meet like minded individuals in which you can collaborate.

I dont want the tenant to feel like they are paying an individual (me) .I would be nice if they also generated a report.2>I want to use a 24/7 service to be available to take service calls from tenant via a 1-800 number and log a ticket.