Welcome to the the addiction..
I think the best time to take lessons is during the day/mid-week. Its less crowded so you'll get alittle better coaching from someone thats not busy watching 15 people. And there wont be that many people to see ya crash. lol
Before you go buying anything other than some gear, I'd suggest renting resort stuff. If you end up not liking the sport, then you're not out hundreds of bucks. Also, wear wrist guards! Busted wrists are a very common injury because its habit to throw your hands down when you fall. But stick with it regardless of how many times you dont think you'll ever figure it out. Good luck bro