I upgraded my MacPro to 10.6.5, IPAD and iPhone4 to 4.2.1 and encountered all sorts of problems before even thinking about jailbreaking. People are losing data, having their (mostly) IPADS lock up, and wi-fi connectivity to the IPAD drop without warning. For me resetting the router re-connected the IPAD for a few hours. I had two boot drive backups so I went back to 10.6.4 and took the IPD back to 3.2.2 and IPhone to 4.1. I re-jailbroke them and they are rolling along smoothly.
Cydia says to hold off on jailbreaking 4.2.1. I suggest not even upgrading your Macs, phones and IPADs. A JB iPhone and IPAD are no big deal. I have blown away the devices back to 'new' status and ther re-JB them with no problems. When I JB the 2nd time the restore to new removed every trace of the JB even down to removing the Folders I had put there to hold images.
For a digital photography equivalent it's like cleaning your camera's sensor the first time; it's unnerving but after a time or two it is not a big deal, just be deliberate and keep track of what you're doing.
Good analogy.