It took me 5 hours (multi-tasking) to finally jailbreak my old iphone. The primary reason I did it was to install Qik, the live video-streaming app. I will ignore the discussion about adding Qik to the iPhone store, plenty of people talking about that. Added bonus, Winterboard is cool, adds a few bells and whistles to the generic iPhone interface, and they seem to have done a good job making it separate from the core code and impervious? to upgrade woes.

My thoughts on the process. Please add yours as a comment. I’m ok with the five hours. Caveats include me making some stupid mistakes (RTFM), the documentation is so-so, the process is convoluted for mere mortals and it takes forever to build the app on my ancient powerbook (which will be replaced with whatever goodness Apple unleashes next month.)

Get rid of the external application. iphone dev team should create a plug-in for itunes if it’s possible.

Create a repository for the .ipsw files – you have to download files to build the application on your desktop, then install onto your iPhone. Remove this cumbersome step of having to download the files and link to a repository, behind the scenes. Protecting user from making bad decisions (props to Vince Vaughn).

Looks like something is in the works to simplify the process, Windows only, best named hack of the year so far, My little Pwnie.