As the owner of a jailbroken iPhone, I have to tell you jailbreaking is WAY over-rated, even more so for the iPad.
Yes, there are maybe a dozen pretty nifty apps out there not otherwise available. Maybe a dozen, only a few of which will be of particular interest to you. I did mine because I moved to another country so I had to "unlock" the phone, and since then I've found a couple or three apps that make my iPhone work better (because it's an old original one). I don't have any interest in having 10 gazillion wallpaper themes, so that aspect of jailbreaking is not important to me.
The main complaint I have about jailbreaking is that the entire (complicated) process must be re-done EVERY time Apple updates the iOS, and sometimes you wait weeks for the "hack" that allows jailbreaking to come out. To me (maybe not to everyone, but to me) that's a royal PITA I don't care to contend with over and over. Luckily, this old iPhone has now gone as far as it can go -- 3.1.3 -- and I'll never have to do the jailbreak/unlock shuffle again.
I have a different perspective on it. If not for jailbreaking, I'm sure I'd have an Android phone right now.
I wrote a little article about my favorite jailbreak apps that I'll post after the jump.
As for all the having to rejailbreak, that assumes you're always updating your phone, which I don't. And the last jailbreak I did wasn't complicated. I went to a website and that's it.
Article:
There are countless possibilities the world of Cydia has opened to those who choose to set their iDevices free from the shackles that Apple places on them. Jailbreaking seems like a novelty until you actually get into it and realize there's so much more your iPhone, iPod Touch, or iPad is capable of that you'd probably never even considered previously. Currently, I have an iPhone 4 running iOS4.0.1, and here's a list of 10 jailbreak apps I consider essential.
1. MyWi 4.0 - Turns an iPhone into a wireless hotspot. Allows you to tether a notebook, iPad, iPod Touch, PSP, DSi, etc to use your phone's data connection. For those of us fortunate enough to have retained the unlimited data plan, largely negates the need for a home Internet connection.
2. Quick Reply for SMS - Allows you to reply to a SMS by putting it on top of whatever else you're doing on your phone (even the lockscreen) so that you can instantly reply to a message and go right back to what you were doing. Admittedly, it was much more important in old software versions because of the lack of multitasking, but it's still invaluable if for no other reason than you can see an entire message without unlocking your phone and waiting for the Messages program to load.
3. SBSettings - Allows you to toggle functions and operations instantly. Also allows you to add a date to the status bar, or hide unused icons from the springboard.
4. Infinifolder - Normal iOS 4 limits you to 12 icons in a folder, with infinifolder, you can add as many as you like.
5. NoLockScreen - Just like it says, eleminates the lockscreen. Press the home button, and you're home. I can't imagine a time whenthe recessed home button could get inadvertently pressed in my pocket, so for me, the lockscreen was a superfluous step in accessing my phone.
6. My3G - Some programs are designed to only work over WiFi. Want to Download an app over 20mb? Want to use FaceTime? Want to watch a full episode from TV.com app? Too bad! You have to have a WiFi connection. My3G tricks your phone into thinking it's on WiFi even when it's on 3G or Edge.
7. Direct Closer Pro - With iOS4's multitasking, to close an app out totally, you have to double click the home button, then hold an icon until they start wiggling, then click on the x to close what you want, then click home again to stop the wiggling so you can select a program to switch to. Folder Closer Pro already has the icons wiggling when you double click home, so you can delete them, OR you can just touch an icon anywhere but the x and it will switch. It saves 2 or 3 steps.
8. Winterboard - Allows you to personalize the aesthetics of your phone. Custom icons and UI, lockscreens, dial screens etc. It's nice to be able to personalize.
9.Syncronicity - When you sync your iDevice with iTunes, whether to backup or just add some music or video, Syncronicity allows you to still use your phone, so no more disrupted syncs because you got/answered a text!
10. WiFi Sync - How often do you plug your iPhone into iTunes and let it backup and sync? I'll bet not often enough. It takes a while, it keeps you stationary etc... WiFi sync is an app you download to your phone and a companion app you download to your computer, and as long as the two share a wifi connection, you can initiate a wireless sync right from your phone. I do it every night as I go to bed.
Honorable mention to Folder in Folder - Pretty self-explanatory, let's you put folders inside other folders. And Folder Closer - When you select something thats in a folder, automatically closes the folder when you return to the home screen.