[Griffinaz]

I am sorry you had all those problems. I have jailbroken several phones and my own has been jailbroken since I got it back in 2007. I have updated it to 1.1.2, 1.1.3 and 1.1.4 and re-jailbroke it every time. I install and uninstall programs daily testing out different software things and other than occasionally getting something like the screenshot program and didnt work right and caused problems I have not had any jailbreak related problems at all. If you back up your phone before doing the jailbreak and you follow the instructions you will have no problems with it at all, as the hundreds of people on this forum that are jailbroken have already proven.
If you go more indepth into the specifics of the problems you had, errors, anything like that then maybe someone can tell you what happened to cause it. You mentioned loosing all the pictures you took from your trip to Boston. If the pictures were only on the phone and you never synced them to your desktop computer and you just updated your phone without ever jailbreaking it you would have lost them anyway. The jailbreaking wouldn't have caused that. If you backed up your phone and synced the images off the phone then they would still be on your desktop so again you would not have lost them. Not sure what happened there but I can assure you, if you follow the instructions jailbreaking will not mess up your phone. Yes, it will void your warranty but again that is in the instructions and mentioned all over this forum so that shouldn't be a shocker to anyone considering doing this.