You need an assistant to click on "Software Update"? Sorry - apart from the bandwidth issue which is somewhat mitigated by Apple making the downloads available locally - its a pretty painless job.
S'a joke
It's my own fault really - I skipped the Leopard update just prior to the release of Snow Leopard
and the little iPhone OS update that came shortly after that, just recently downloaded iTunes 8.something now need to download 9... seeing all of the new updates just makes me feel more 'dated' (I know you needn't increment your way up and that applying the latest will suffice...)
Also: updating a jailbroken iPhone is a spot of hoop-jumping. Again, admittedly: my own fault / choice.
Being 'ex-Windows' also fills one with trepidation at the prospect of an update - updating a Windows system is a leap of faith... against the odds.