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

If not, are you just looking to gamble?

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 have been presented with  an off market deal in the Clinton Hill/ Bed Stuy border in Brooklyn

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.

I have investments in the Chicago area, Indiana side of the border though.

I just don't see the same potential for East Boston and I would stay far away from the Chelsea border, that is in my opinion the last area to appreciate there.

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.