Jailbreaking certainly gives you access to 'hidden' system settings, and is fantastic for that. Custom themes, multitasking (real multitasking), etc.
Jailbreaking also gives you access to 'app stores' where you can get fee-based software for free. Cydia is an example where you can get both paid and free apps...and apps that would cost $$ in the app store and are free on Cydia. It is also a place for developers to go and 'sell' their apps when they've been rejected by Apple.
I know of quite a few people w/jailbroken 3Gs phones, all of which have 'paid' apps they downloaded for free. It's easy, so why not do it?? I have these discussions w/my friends all the time, about the moral issues around jailbroken phones and app stores.
I don't mean to hijack this thread, nor cause a long discussion, I should have phrased my language better... "when you jailbreak it and
download software for free that normally costs money in the regular Apple Store, you are stealing from someone...not in the 'microsoft sells office on a $1 DVD for $500 so I'm morally ok with it' stealing, but 'This guy/gal sells his app for $1 but we'll get it for free anyway' stealing...hey I'm a huge torrenter, but if you find something you like, throw some $$ the developers way, just sayin' ya know??"
My point here is not 'jailbreaking is bad' heck I'd do it if I had an iPhone/iPad, and I'm constantly hacking Windows stuff, BB stuff, etc (PC, phone, you name it)...my point being there are lots of small developers out there selling their stuff for a buck in the App Store...if you get it for free via jailbreaking, at least send them some money for their efforts. I have no idea on how much revenue they lose to this, but even a few bucks to a small developer is a lot
Sorry for the hijack, back to your normally scheduled Apple discussions
As for redbeards question, I'm not sure about the iPad jailbreak, but the regular iPhone jailbreak allows you to sync like normal. I think the new iOS4 does not have a full jailbreak yet, so if you buy a new iPad w/iOS4, it is not jailbrbokenable yet (the iPad jailbreak has to have the original OS3.1, which they have broken up to iOS4, but you can't start out w/iOS4, does that make sense?)