I haven’t jail broken a phone since the 3G, I just don’t see a compelling reason to anymore. The reason I did it then was to get around the tethering restrictions that att had at the time, but now I can’t really think of any features that I would want my phone to have that it doesn’t already.
I thought you could sideload self-built apps onto an iPhone these days. I mean, it has some restrictions, but at least it doesn't require forking over $99.
It's simple but I'd like ssh to phone home. I don't see a reason to trust an app. Otherwise Apple put in most everything else I used (like SBSettings etc).
I'm assuming most jailbreakers probably don't want to enable piracy, but just want to use apps that Apple won't compete with fairly - like Steam game streaming, or a browser built with an alternate engine like chromium.