I have SFRs in KC, so probably leaning towards somewhere in midwest.

It doesn't sound like you have any definite goals besides buying a new home so in the absence of that I'd lean toward selling.

I know that leaning on the idea of appreciation veers toward speculation, but in Westchester its a pretty good bet that the property will appreciate pretty significantly. 

I am a 23 Year old business owner who is exited and yearning to lean how to be a Real Estate Investor. 

I am leaning towards buying a ticket and attending the event, but just wanted to confirm with some people who may have been before that it is in fact worth the $300?

Although I have friends and relatives in the areas mentioned above I can't lean on them for the day to day management and maintenance of my future properties.How did you acquire your first property manager? 

Should I lean towards the job that would get me closer to the RE industry?

I own a couple mutli families in Bakersfield and those have been good cash flowers over the years so I definitely tend to lean in that direction.

I'm willing to sacrifice my time, body, friends, and sadly, family as I work to save up for my first purchase.

In my area you dont have to be a GC to buold your personal home.Find a local bank to work with on construction loan (I would suggest you get a account for that bank and donuts always help) Get a list of your area governing body on what is needed to be submitted for approval.