Hey Chaz-
You've come to the perfect place to get some of your questions answered. Obviously, learning how to snowboard can be quite the challenge. The first couple of days will no-doubt be rough. From what I hear, it's very important to give it at least three days before you even consider giving it up. You will fall a lot, but you have a breakthrough on that third day. You'll probably want to take a lesson that first day. I also recommending learning on powder days. When it's powder, the falls won't hurt. But keep in mind, powder can be quite tiring, too. But it's a blast.

All of the resorts have great snowboarding instructors and programs. For your first time, I would recommend hitting up the smaller resorts(Loveland/A-Basin), that way you are less likely to deal with huge crowds of people getting in your way.

As for equipment, go to Breeze ski rental. They have a demo pass for $189 a year. Otherwise, renting everytime will probably cost around $40-$50 each time. That gives you unlimited access to all of their demo equipment all year. This gives you a chance to try out so many things. By the end of the season, you'll know which board you loved the most, and then you'll know what you want to buy.

And when it comes to meeting people, try skicarpool.org. I have met so many people using this site. It's incredible. It's also great, because you can share gas! I started using the site last year, and have made several friends that I still talk to.

I can't really answer your workout question, just because I am a skier. But as a skier, stairs and lots of cardio helps me stay in shape. If you have any more questions, feel free to ask. I hope you have a great time learning to board! You'll love it!