I can't say anything particular about cPanel - if it relies on server programs installed from FreeBSD ports then you'll have to recompile those. It it's linked to base libraries found in sixth release, then you'll have versioning problems. FreeBSD has an extremely stable ABI/API and there's a big chance that you can fix those by just using symlinks to newer version of the libs. But it would be smarter, in this case, to install cPanel that's linked to 8.2 libs.
It shouldn't be more than one hour, for a single major version update via freebsd-update. If it's really essential for you to have minimal downtime and update that server, as opposed to migrating userland to a new server, this is what I'd do;
- install both 7.4 and 8.2 releases inside virtual machines (on desktop)
- compile all ports you have on production server, and make packages, on both 7.4 and 8.2 system
- test cpanel binaries on both. that means physical copy of all files off production server
- if it works, great. if it doesn't, mark all steps necessary to make the 6.4-7.4 transition work, and then transfer program from 7.4 to 8.2, and mark all steps necessary to make it work on 8.2
- script those steps. use virtual supervisors' snapshotting abilities to retain testing states.
- freebsd-update from 6.4 to 7.4. install kernel updates. reboot. install userland. remove all ports and install precompiled packeges from step 2 for 7.4. finish update and reboot.
- run the script, if you need to.
- at another scheduled 1 h downtime, repeat steps for 7.4-8.2 upgrade