I remember some of that. I didn't really get into the jailbreak scene too deeply, though. Usually, what happened is I heard that some Thing I wanted to do that

I remember some of that. I didn't really get into the jailbreak scene too deeply, though. Usually, what happened is I heard that some Thing I wanted to do that you couldn't on iOS was available if it was jailbroken -- "tethering," for instance, back before that was added to iOS. I'd jailbreak the phone (which could be really easy or involve a lot of hoops to jump through, depending), and install Cydia, and install the App That Did The Thing. By that point I was usually already frustrated because the whole user experience of the software from the jailbreak side of things tended to be noticeably worse. (I'm sure there were exceptions, but in general, that was consistently my experience.) Then I would discover that the App That Did The Thing was a little buggy and not very well designed, and sometimes didn't even consistently Do The Thing, and I would look around the Cydia store and discover that there was very little other stuff that I actually wanted, and then something would crash in a way that took the whole phone down in a way that official iOS apps very, very rarely do, and I would say "enough of this" and put the phone back in jail. tl;dr: I tried to be adventurous, but was too impatient. :)