On the VSS side, there are conversion tools that are available to help with migration. They can mostly maintain version history (there are caveats that are explained in the readme and docs). I have migrated well over 50 VSS projcts into perforce using the VSS to perforce tool. Getting the data out of VSS can be a bit finicky and not terribly speedy, but it works. If you have direct access to the disks (i.e. not over a network share) to the VSS repository, the conversion can go much quicker. You can find information about the scripts here.
There is a simlar page for CVS to perforce conversion here, although I don't have direct experience with that. These links are good places to start. You can also search through the Perforce mailing lists at the Perforce Knowledge Base located here. I'm pretty sure that you might find some conversion information in the mailing list archives.
Migrate your old projects first. You can make sure that your process works. When we migrated active code to Perforce, I took one weekend and basically took down access to the servers and moved the code over to Perforce. Honestly, it was a pretty easy migration and when people came back on Monday they were ready to go. You might think about preparing your employees with Perforce cheat sheets after you start doing the migration.
The biggest gotchas might actually be preparing your people to use Perforce. Had I done it over again, I would have migrated our smaller active projects first and prepared smaller numbers of people to use Perforce at once. As it was, I had to train 120+ people on day 1 after the migration and that was a bit much. Also, make sure that you don't have 100+ people hitting your server for a fresh sync on day 1 either. We wound up taking our server down multiple times during the first few days. We used a windows 32 bit server which I would not recommend. We have a windows 64bit server now and it's much more robust. If you can, I would actually use Linux as your OS for your perforce server. Again, there should be good info on the Perforce site about performance.