Hi, johnnychimpo:
Yep, it's actually that simple. Upgrade to iOS 5.0.1 and then apply the redsn0w jailbreak. However, in preparation for your upgrade, may I suggest some things:
1) Make a backup in iTunes for your email, contacts, etc. This will ensure you don't lose all your data and settings.
However, since you are moving up two major releases (from 3.x > 4.x > 5.x), I would
not recommend using any backup package to save your Cydia tweaks. There have been HUGE changes since 3.x and any time you move up a major upgrade, it's best to do a fresh install of the firmware and NOT use backups. They just don't keep up.
So, I'd recommend you make a list of your Cydia tweaks and then, when you are jailbroken, go to Cydia and re-install them, a couple at a time. Yeah, it's a bit of a pain, but it will save you headaches in the long run. And, Cydia is like the App Store in that, once you buy a tweak, it's yours and you can re-download/re-install for no charge.
2) Download the 5.0.1 IPSW from our official link (here:
http://www.ipadforums.net/ipad-hacking/24939-official-apple-ios-firmware-download-links-ipad.html) or from Apple. Remember where you saved it and, if it downloads as a .zip file (cause you used Internet Explorer) - don't unzip it and change the extension from .zip to .ipsw.
3) Put your iPad into DFU mode to do the restore (with the iPad connected to your computer but iTunes closed). It works best on iPads that were already jailbroken if you do this (versus "merely" hitting the restore button in iTunes without being in DFU mode). You probably know how to do DFU mode, but, just in case:
http://www.ipadforums.net/ipad-hacking/27489-dfu-mode-dummies.html
4) Once you are in DFU mode, iTunes should open and tell you it's detected a device in restore mode. Accept that first notice. Oh, and if iTunes doesn't open - open it once you are in DFU mode...
5) Once iTunes has detected the iPad as needing restore, press and hold the Shift key and click on the "Restore" button. You'll get a Windows Explorer window for you to browse and find that .ipsw file you downloaded. Select the file and then let iTunes do its magic.
6) Once it's done putting iOS 5.0.1 on your iPad, select "restore from backup." This is the point where you'll get all your email, contacts, etc., info back. Remember, this is just the App Store stuff, you emails, contacts, songs, etc.
Once iTunes is done restoring from your backup, you should be on iOS 5.0.1
8) Then, you can jailbreak it with the most recent redsn0w program as mentioned in this thread:
http://www.ipadforums.net/jailbreak...orial-jailbreak-ipad1-ios5-using-redsn0w.html
9) And, once that is done, off you go to Cydia to get all your "stuff" back.
That should do it. Yep, it'll take some time (maybe even a LOT!), but, you should be good.
Hope this helps and please, let us know how you get on or if you have any [more] questions. Good luck.
Marilyn