Hey man! Welcome aboard! It's.. going to suck, but uh, yeah! Go Jays!
First thing I could recommend is to pick up some light reading on baseball. Give this site (link) a read. It gives you a good idea about the basics of baseball.
After getting comfortable with that, I would pick up a few books like some autobiographies or novels on the sport. There are a LOT of good ones.
When you're comfortable with the basics of baseball, check out Fangraphs. Here's the glossary section (link). Someone in this thread said that fangraphs isn't easy to understand for people who don't know the stuff but that's just not true. I spent a good two hours reading that site one afternoon when I had nothing to do and it explained everything for me. My view on baseball changed. Some of the stuff on fangraphs is incredible.
Shameless plug: Breakingblue.ca is a great baseball blog that you should absolutely check out. Fangraphs, BlueBird Banter, Tao of Stieb, and Sportsnet all have great blogs.
Buy MLB.tv. It lets you watch games anywhere, any time, for just $100. It's incredible. HD, split screen, quad screen, everything. It's great.
Play some of the sport, too. I'm actually heading out for a game in an hour. It's a very fun sport to play and it'll help you learn.
To answer your questions directly, some good books include:
The Book - Tom Tango
Moneyball - Michael Lewis
Shoeless Joe - W.P. Kinsella
Ball Four - Jim Bouton
The Bullpen Gospels (and the two sequels) - Dirk Hayhurst
I Never Had It Made - Jackie Robinson
Calico Joe - John Grisham
Movies:
Field Of Dreams (based on Shoeless Joe)
Bull Durham
A League of their Own
Bad News Bears
The Sandlot (1 is mandatory, 2/3 are optional and terrible)
The Natural
Eight Men Out
Pride of the Yankees
Major League (1 is mandatory, 2/3 are optional and terrible)
For Love of the Game
Moneyball (movie form of the book)
Rookie of the Year
That should keep you busy.
And about question 2, I guess pubs and such, and I know guys from the board often meet up, but I'm not the best person to ask lol.