If I switch the sim from my 8800 to the pearl will my contacts follow with it or do they stay on the phone itself?

Wirelessly posted (8700g: BlackBerry8700/4.1.0 Profile/MIDP-2.0 Configuration/CLDC-1.1 VendorID/100)

If they are stored on your SIMN then yes.

It depends on if you have them stored in the phone memory, then no, not automatically. To switch BBs, use the latest version (4.2, Service Pack 1) of Desktop Manager (download from www.blackberry.com) and use the Switch Device Wizard, or backup your old BB with DM and then restore the address book.

Good luck.