I just got an iPad 1 with iOS4. I just jailbroke using jailbreakme.com - Worked great. Now before I start installing apps, should I just go ahead and update to iOS5? It seems like a lot of people have problems updating to iOS5. Note that jailbreaking is important to be since I like to customize the environment. Will I run into any issues on iOS5 with Jailbreaking?

A quick answer would be VERY MUCH appreciated - we're doing the Daylight Savings switch in the US tonight, so I have an extra hour to mess around with the iPad! Thank you!

If you don't mind the tethered jailbreak I saw go for it. I upgraded and haven't had any issues at all. Just remember that not all cydia apps work use iOS 5 yet.

If you are a die-hard untethered freak, don't do it.
Apps and tweaks are slowly getting compatibility, but not everything works yet.

Just find out if the tweaks and apps you use are fully compatible with ios 5. And if they are, and you can handle a tethered jailbreak, (and a lack of iBooks), then go for it.