I was thinking that if I could find a place close enough to public transportation, I could cut down on my living expenses utilizing the aforementioned owner occupied multifamily home strategy, while maintaining low transportation costs. 

We also need the cashflow monthly to maintain our lives or build our "Property Business".  

I don't want to risk selling "junk" to an investor, even though the bank said they're very well maintained.  

My tenant and I do maintain a good relationship.

and only when you understand this should you map it to a strategy that is in line with your unique skills and motivations3) You will need discipline and an execution plan - being your own boss is great but you also need to figure out how to be your own best employee4) Define a plan and set interim milestones - being an entrepreneur can be a lonely profession and success is not a straight line so plan for getting yourself some small wins and maintain a long term perspective to help get you past short term challenges.5) Understand what constraints leaving full time employment will eliminate e.g. more time to focus on real estate, and what constraints it will introduce e.g. less income and ability to get credit6) Understand that you will need a team to succeed so make sure that the people in your life on whom you depend on for support are fully behind youHere is an article that I wrote that might be of additional help - https://www.biggerpockets.com/member-blogs/11782/88425-want-success-here-are-ten-things-you-must-give-upGood luck, going on your own has got enormous upside potential but it is not pain free.

My neighbor is selling his home and the VA home loan that the new buyers are getting is requiring me and my other neighbor to enter into contract to maintain our road.Here's the deal:  I live in a nice neighborhood and on a private drive off the main road.  

At 19, you need to know that whatever industry you choose to work in, education will be vital, it is a never ending quest that requires you to maintain proficiency and to stay current with business requirements.

If it appreciates its an added bonus but at minimum as long as the house maintains value during sale date, thats considered a good return? 

Yearly inspections by city, help make sure this type of equipment is properly working so landlord can maintain rental license, Not all cities do yearly inspections.

Scaling my current business is my main priority right now, so I don't need the stress of maintaining the RE license at this time.