Went through with BB techs and we saw all kinds of errors in the events log of the BES server. All kinds of group policy errors and things saying it couldn't access the SMTP server or the SQL database. I noticed in TCP IP there was an out of date DNS server so I updated that and rebooted. It came back up with some of the same errors but after about 5 minutes all the errors ceased, and everyone started calling saying their Blackberries were working and asking "did I fix something"? The BB tech had never even seen these errors before EVER, so it was a learning experience for everyone involved.
Also, the user in question somehow didn't have wirelessly syncing memo and contacts. When you hit Options under each of those it didn't have the "Wireless Sync - Yes" line available. A wipe of the device and resync with BES seemed to fix that issue specifically.