Jailbreaking my iPad was the very first thing I did, just as it was with my iPhone. By now it's become a 1 step process and "I don't know if I can..." is no longer a viable excuse.
First I hit up the Cydia store and grabbed a few free, cool mods including winterboard for theming my device (I don't like labels on my dock icons) and dashboard which is a cool panel that brings up your widgets from wherever you are. I also got some free mods that solve some of the limitations of the device. Backgrounder now gives me seamless backgrounding of apps, Activator allows me to enable backgrounding and dashboard with a variety of gestures such as pinch, and swipe down from statusbar.
Also! Safari download plugin will allow you to download most file types right within safari. Pair it up with ifile, and now you can browse your device to use those downloaded files. This means you can download mp3's and play them all on the device, no touching iTunes. I'm not even going to go into things like sbsettings, dtunes, pwntunes and so much more. Besides the fact that the whole thing is 100% reversible in ~10 minutes....
Bottom line: If you're not jailbroken, you're missing out. Trust me.
I have two concerns with jailbreaking. Perhaps you can help make them go away :)
Originally Posted by Deenybird
1) Loss of data: I know I need to backup before jailbreaking and my data will be preserved in case I have a problem and need to reset. The concern is really more for reversing the jail break. If I use it for a few months and then want to reverse it do I still keep my application data (e.g. saved games)?
2) I've read stuff about having to back up some sort of iPad ID using a server or something. What is the situation that would make that important?
EDIT for 2 it looks like this step is to avoid being unable to revert back if you are upgraded to a new OS that is not jail broken.