Im new to this also but learning the ropes at an accelerated pace. I had my ipad now 2 weeks. Last wednesday, i took da plunge like $&@? It, amd went to jailbreakme.com. My ipad is 32GB wifi ver. 3.2.1. It was soooo easy jailbreaking on dat site, at least for me. Once u go to the site, u gnna see a slider. Slide it to jailbrake n u good to go. It downloads and installs, then u get the Cydia store app. This is where u go to get jailbrake apps.
Id say go for it but just make sure u do ur research first. That ssh thng u talkin bout has to do with the ipad software version or somethn. When u jailbrake, go to cydia app, there u can have cydia store those ssh details and such. This is for if u need to restore to specific firmware, if uve upgraded on accident or somethn. Im luvn this ipad. Im multitasking like a mofo now. Downloading videos straighT to ipad without need for itunes. Got the new bt mouse stack. Stock, the ipad doesnt accept or have the drivers for that. When u jailbrake n get bt mouse stack, u can use it now. Soo many different cool useful apps. Make sure ur apps r ipad only or ipad compatible. Or else ur device might start acting up. Get winterboard also from cydia, lets u customize the interface/themes and change icons n stuff. Really in depth. Im amazed with it. I have kive wallpapers now. ;-). Other apps to get backgrounder(for multitasking), citurious(compliments backgrounder, a task switcher, wrks really good), fullforce(allows iphone apps to be forced to ipad resolution), quake 3, n more.
If u go for it, to be on the safe side, make sure to backup ur ipad by syncing itunes on desktop.
Aint it crazy how we dont even have our devices long n lust for cracking them open..lol. I masterd this ipad, jailbrake. Have android os on my windows mobile tilt2..dual boot into android or windows mobile. Plus tethered to my ipad thru wifi using xdatethering app on my phone. It cant get no sweeter. I really misjudged this ipad at first b4 i got it. Now this is the best, coolest device i have. Replaced my computer basically.