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Why would you jailbreak an iPad?
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in a word, control.
do you want your ipad to look and perform the way you want it to or the way apple wants it to?
first post and you didn't even bother using the search. that's the point.
type 'why jailbreak' in the search function and 172 results came back in the ipad forum alone. too lazy to do that? here are some results that specifically ask 'why jailbreak' in the subject line
https://forums.macrumors.com/threads/1028333/
https://forums.macrumors.com/threads/910656/
https://forums.macrumors.com/threads/982608/
https://forums.macrumors.com/threads/888708/
https://forums.macrumors.com/threads/979756/
https://forums.macrumors.com/threads/939766/
https://forums.macrumors.com/threads/922932/
https://forums.macrumors.com/threads/909541/
happy reading. THEN come back and ask a question.
type 'why jailbreak' in the search function and 172 results came back in the ipad forum alone. too lazy to do that? here are some results that specifically ask 'why jailbreak' in the subject line
https://forums.macrumors.com/threads/1028333/
https://forums.macrumors.com/threads/910656/
https://forums.macrumors.com/threads/982608/
https://forums.macrumors.com/threads/888708/
https://forums.macrumors.com/threads/979756/
https://forums.macrumors.com/threads/939766/
https://forums.macrumors.com/threads/922932/
https://forums.macrumors.com/threads/909541/
happy reading. THEN come back and ask a question.
You can't make something from nothing. If your ipad isn't getting data from a wifi hotspot or AT&T's 3G, you can't transmit data from the ipad. Learn some critical thinking skills. 
Surely it takes more effort to enter the thread, read the OP and post a response, than it does to read the thread title, and simply move on?
Anyways, getting back on topic, the only primary reasons I have for jailbreaking, are SBSettings(Brightness), Backgrounder, and Browser Changer(iCab).
with 4.2, Browser Changer alone won't be reason enough to jailbreak, but if it's easily done, then I see no harm in doing so.
I'll bite since I am waiting on the 4.2 jailbreak as my 4.2 iPad sits on my desk at home not being used.
Let's start with the basics:
1) MyWi. The iPad has amazing battery life and MyWi combined with unlimited 3G makes it the perfect replacement for a MiFi device. I have been able to tether through my iPad for 8 hours straight still having plenty of battery life remaining.
2) My3G. This application is very simple. It tricks applications into thinking they are connected via wifi instead of 3g. Ever want to download a program from the App Store via your iPad only to be told to connect to wifi? This will solve that problem.
3) SBSettings. This gives you a single tap interface to toggle things like wifi, 3g, bluetooth, etc. It also provides at a glance access to the device IPs, remaining memory, and others.
4) Remove Recents. This helps clear the multitasking menu on the iPhone and iPad to remove all applications that are not paused or running in the background.
5) Backgrounder. This gives you control over how and when applications are backgrounded.
6) iOS VM Hack - Google it, but it makes my devices much more useful in my opinion especially with backgrounder.
7) iFile/OpenSSH/Filesystem access - Ability to copy files directly to the filesystem.
8) iAdKiller, Ad blocking hosts file, Safari Block etc - Block ads on your device.
9) NoAccessorySplash - Removes the popup when connected to devices it doesn't think are compatible.
10) PrivaCy - Google it. Increases iOS privacy by disabling phoning home for certain programs.
11) PushMod - Set the check interval for email under 15 minutes (1, 5, or 10 minutes)
and these are only the few I find the most useful. You will likely find a good deal more that will help your device become just the way you want it.
Let's start with the basics:
1) MyWi. The iPad has amazing battery life and MyWi combined with unlimited 3G makes it the perfect replacement for a MiFi device. I have been able to tether through my iPad for 8 hours straight still having plenty of battery life remaining.
2) My3G. This application is very simple. It tricks applications into thinking they are connected via wifi instead of 3g. Ever want to download a program from the App Store via your iPad only to be told to connect to wifi? This will solve that problem.
3) SBSettings. This gives you a single tap interface to toggle things like wifi, 3g, bluetooth, etc. It also provides at a glance access to the device IPs, remaining memory, and others.
4) Remove Recents. This helps clear the multitasking menu on the iPhone and iPad to remove all applications that are not paused or running in the background.
5) Backgrounder. This gives you control over how and when applications are backgrounded.
6) iOS VM Hack - Google it, but it makes my devices much more useful in my opinion especially with backgrounder.
7) iFile/OpenSSH/Filesystem access - Ability to copy files directly to the filesystem.
8) iAdKiller, Ad blocking hosts file, Safari Block etc - Block ads on your device.
9) NoAccessorySplash - Removes the popup when connected to devices it doesn't think are compatible.
10) PrivaCy - Google it. Increases iOS privacy by disabling phoning home for certain programs.
11) PushMod - Set the check interval for email under 15 minutes (1, 5, or 10 minutes)
and these are only the few I find the most useful. You will likely find a good deal more that will help your device become just the way you want it.
Jailbreking is NOT a way to get "FREE" (A.K.A Stolen/Cracked) stuff. Jailbrekaing give you Full control over your device (Since Apple think that users are so dumb that they sandbox us into this userland jail so we don't mess up anything - and to tell the true they are right most of the time
). Jailbreaking is the act of getting root access to the device by “escalating user Privilege”, Privilege escalation is the act of exploiting a bug, design flaw or configuration oversight in an operating system or software application to gain elevated access to resources that are normally protected from an application or user. The result is that an application with more privileges than intended by the application developer or system administrator can perform unauthorized actions.
In iOS the user only have access to an specific area (commonly know as “Userland”) by the mean of a CHROOT jail, breaking out of this limitation allow regular user to scale to “root” (yielding the name Jail Breaking).
You can read more about it here: Jailbreak FAQ and commonly use Terminology + Guides
Why to do it? well when i got "FULL" control over my device when apple say no multitask until they release an update, I I am multitasking all my app, when they release 4.2 and they say that "only" a few app can multitask, I can make "all" my apps do it. When they say that my iPad cannot out to a monitor, i can do it, when they say that only the iPad cable will work, I am using $2 cables that i got from Monoprice. When they say that my lockscreen need to be useless with no infomation, I am displaying my Twitter, my Calendar and MAcrumors and TUAW rss feeds, etc, etc, etc. The point is that "I" am the one who decide what and where to do what i want and no Apple. It is my device so I should be able to install/remove/modify it as I want.
I think iFile would be the biggest reason I would Jailbreak. I want to be able to have control of my file system with the ability to save and move files.
Also, I want REAL multi-tasking. Not a glorified quick launch bar.
Also, I want REAL multi-tasking. Not a glorified quick launch bar.
The main reason I jail broke mine was so I can have it looking how I want, why should Apple dictate that I should only be able to have six icons in my dock?, why should I waste all that screen space when I could fit twice as many apps on my screen?, I don't like grey so why shouldn't I be able to change the colour of the text for the apps name. It's my device not Apples so I'll have it looking how I want.
So now I've removed the lock screen so it's instant on, I've put nine icons in the dock and the dock also scrolls so I have another nine icons on my second dock 'page'. On my main springboard page I have no apps visible at all, vie hidden them all with iblanks so I can view all my wallpaper fully. For my top 18 apps I use the dock then for stuff I don't use everyday I have those underneath the dock, so instead of swiping from the right to move onto page two I swipe up the screen to bring the apps up from the bottom. I have my iconoclasm set to 6x6 or something like that, something that looks good in both landscape and portrait. I do have a page 2 of apps which is dedicated to just games, my games screen scrolls also so there's no limit (until my 16gb is full lol) as to how many games I can put on that screen. So now need at all for me to have more than two screens.
I'm really pleased with my layout now, I wouldn't buy a new iPad that couldn't be jail broke, Ive not got into altering themes, apps graphics, fonts etc so with the right cydia programs it takes like 5 minutes to set it up, though it did take me three weeks to decide just how I wanted things laid out, though once I had decided I've never changed it. No need for folders either, with all oft used appsnin the dock and games on page 2 I don't need ugly looking folders when all they do is introduce an extra button press into the equation.
So now I've removed the lock screen so it's instant on, I've put nine icons in the dock and the dock also scrolls so I have another nine icons on my second dock 'page'. On my main springboard page I have no apps visible at all, vie hidden them all with iblanks so I can view all my wallpaper fully. For my top 18 apps I use the dock then for stuff I don't use everyday I have those underneath the dock, so instead of swiping from the right to move onto page two I swipe up the screen to bring the apps up from the bottom. I have my iconoclasm set to 6x6 or something like that, something that looks good in both landscape and portrait. I do have a page 2 of apps which is dedicated to just games, my games screen scrolls also so there's no limit (until my 16gb is full lol) as to how many games I can put on that screen. So now need at all for me to have more than two screens.
I'm really pleased with my layout now, I wouldn't buy a new iPad that couldn't be jail broke, Ive not got into altering themes, apps graphics, fonts etc so with the right cydia programs it takes like 5 minutes to set it up, though it did take me three weeks to decide just how I wanted things laid out, though once I had decided I've never changed it. No need for folders either, with all oft used appsnin the dock and games on page 2 I don't need ugly looking folders when all they do is introduce an extra button press into the equation.
There are reasons to Jailbreak your iDevice. But for the Uninitiated Everyday Joe it is probably not worth the effort.
My reasoning to Jailbreak is to tweak the user interface to my liking.
Having a jailbroken iPad helps me search for thousands of existing threads in MacRumors more efficiently.