I have a good deal of experience in 5.5 >> Ex 2k upgrades. There is more than one way to do it.
To be perfectly honest with you, it's not the sort of job you are going to want to tackle without lots of background and documentation. I would consider myself fairly strong with Active Directory, Exchange 5.5 and Exchange 2k and there were still things that stumped me the first time I did an upgrade.
You need to know and understand the Active Directory Connector inside out. There are also numerous "gotchas" that you have to prepare for.
I've done upgrades a couple of ways. One method is the inplace upgrade... more suitable to a smaller, single mail server. I've had the easiest time with a second method, building a new Ex2k server and adding it in to the exisiting Exchange organization. Assuming you have the ADC under control, you can then simply move the mailboxes on to the new server.....
Either way, what I have described is a vast over-simplification of the processes involved. There is a tonne of documentation available to help you with this sort of thing. I would recommend doing at least a weeks worth of reading and two trial runs in a lab before you move ahead with it. There are all sorts of things that can happen.
5.5 >> 2k upgrades in production environments seperate the men from the boys. You can do it, but prepare properly. Do your reading , do your testing, and then move forward when you are ready. Don't rush it.
When you are finally ready to move through it get started, and when you have issues, post them here. It's much easier to answer specific problems then describe the lengthy and complicated process of the upgrade.
Good luck!