Since I don't consider using SSH "fiddling", I don't know what you mean, and I'd guess that most developers don't think twice about how to use SSH. (If they did, they're not much of a developer in my book).
It's ironic to me that the most difficult part was having to jail-break my iphone. Apple certainly doesn't make my life any easier.
I disagree. To me, the jail-break is just a default, one-time requirement to gain control over a device I own. It's actually not too difficult, so I don't consider it fiddling.