Windows Update For Crumblies?

I have tried to drag my older friends into the 21st century - I have had only moderate success.
A couple of them are resolutely holding out regards even trying to use a computer as they firmly believe that texting is technologically advanced enough for them.

And over in the other camp of happy button pushing crumblies, we have one or two 'moments'. Very recently I received a phone call from one of them -

'I've switched my machine on but something's not right.'
'OK, what's the problem?'
'Well I can see the Kewlbox games but not Real Arcade.'
'It should be on the quick launch at the left of your taskbar'
'What?'
'The bar at the bottom of the desktop' ... 'On the monitor' I quickly added, realising she could well be looking on her desk.
'I haven't got one. You know, I thought something was missing.'
'Oh right, Windows hasn't loaded properly. OK, press the start button on your keyboard, it'll say start or have a picture like a window.'
'Keyboard?'
'Take - the - cover - off - your - keyboard.'

I talked her through turning it off rather than doing a restart because she's using Millennium Edition and the menu is slightly more archaic than its successors, I knew she'd be phoning me again later to tell me that she was going round in circles and couldn't switch off with just one restart.

'Right turn it back on'
'The button on the big box?'
'That IS your computer ... yes!' through gritted teeth.

She got it back on - with the taskbar. I talked her through making a shortcut and drop it on the desktop - and how to delete the half dozen extra ones she made. I had to go and lie down after that, I find it very stressful trying to remember ME for one friend, XP for another when I'm firmly in the Vista camp with the others.

I am currently trying to get the ME user to upgrade, especially as she has bizarre notions of going on the Internet - can you imagine the fun I'll have teaching her that when after only 5 years she still has to look for her start button ...