This is by far the most useful drop in tutorial I've ever found.
http://snowboarding.transworld.net/1000095158/how-to/how-to-build-a-drop-in-ramp/ It'll probably cost $100 and it'll be more than legit enough, plus extra portable so you can fit it in a car with a decent trunk instead of a pick-up. Water and salt the take off; you don't want to have to keep fixing it up throughout the session. Lots of shovels. On your first few sessions, don't bother shoveling snow off the stairs. It's still legit to hit urban when there's snow on the stairs, and if you really need a good shot, wait until you have the rail down and then shovel the snow.
I love the hot chocolate idea, that would be such an awesome pick me up for a bunch of dudes helping out.
As far as balls, it really is scary the first time hitting urban, no matter how hard the rail actually is. Just start off with a basic down rail with minimal consequences and be confident. As long as you focus on hopping up on the rail, sliding off the side is the least of your worries! Lastly, I just built a little portable take off so I won't have to worry about building a decent take off with minimal snow. Best of luck, it feels awesome to have some urban on your resume, and if your with a bunch of your good friends it will be fun as hell and the stoke factor will be off the rictor