But I have read and feel that that is almost like gambling.

If not, are you just looking to gamble?

I have considered looking for reale-state jobs so I can really immerse myself in the industry, but I don't even know where to begin and I'm not sure if my tech/marketing background can really help me land a job. 

I used to live near Pasadena and absolutely LOVE the charm of all those historical craftsman homes, especially the Gamble House ... unfortunately, this was before I became a RE investor.

I knew I was gambling when I mentioned money but I've seen plenty of posts asking for advice and only receiving welcoming messages with no substance so I wanted to get some response, even if it was just fishing. 

I use my car for a lot of personal and a lot of business use as well - however, I would not be willing to gamble that I use it more than 50% for business - we do ALOT of road trips year round.2.

Hi all.I want to further immerse myself in RE by finding a meetup closer to my home.

This is my last year of school and am starting to educate and immerse myself in the real estate industry.

In fact you will be in a position where you will need to keep feeding the beast from a thousand miles away to not lose your total stake.Or everything could work out perfectly but do you really want to gamble on that?

I've seen writing contests for properties but never a raffle which would (in NYS) be considered gambling (games of chance) and also involving US Postal service which gosh they have rules about all sorts of stuff you can/can't do via mail.