If I jailbreak to Cydia will it allow me to just drag and drop images to my ipad2 without it having to sync and over ride everything since I use mutliple computers? Or if not, any ideas or suggestions? Thanks!

Yes. But it is not as easy as a flash drive.
Do you want a tutorial?
The reason I ask is because tutorials are long and hard to make so I want to ask before I do all that work.

phonedrive
no need for jailbreak
but

YES omg a tut would be awesome! And would it work going from PC to MAC as well? THanks Graywolf!

Ok, tutorial.

Download openssh from Cydia.
Download winscp for windows http://winscp.net/, or cyberduck for Mac. http://cyberduck.ch
In the username box goes the iPad's ip address. (you can find that in settings, wifi, tap the blue arrow next to the network you are connected to)
Password is alpine.
Now, from the computer with winscp or cyberduck, just drag and drop pictures into the iPad.
To make the pictures show up in the photos app, download ifile from Cydia and open ifile.
Scroll down until you see your pictures. Tap the blue arrow next to a picture. Scroll down to the bottom of the window that pops up and tap "add to camera roll". Then just swipe and delete the picture.

Originally Posted by Poser

phonedrive
no need for jailbreak
but

This is for wireless fun.

And if you have a Mac and wanna do the tutorial above wirelessly, without those apps mentioned, just get netatalk from Cydia.

Originally Posted by Poser

And if you have a Mac and wanna do the tutorial above wirelessly, without those apps mentioned, just get netatalk from Cydia.

I've never had a Mac so I don't know.

Thanks guys I will try it