This Christmas I bought an iPod Nano for Elyn and ran into a lot
of software ugliness.

First, her computer runs Windows 98, and, apparently, cannot be
upgraded to some more recent version of Windows. That sucks, but is
apparently unfixable. Naturally, iTunes doesn’t support 98. Some
sites on the web suggest that, perhaps, you can apply some hacks,
attach an iPod to the machine and use some software to copy music over
— but even then iTunes won’t work.

Of course there isn’t a Linux port of iTunes (too bad for us it
isn’t written in Java…).

I tried both Wine and CrossOver Office — the latter
can actually run iTunes, but unfortunately still does not support
connecting it to your iPod. It might be possible to do what I want
with some combination of iTunes, a program to remove the DRM from the
downloaded songs, and some Linux-based iPod program like gtkpod… but
this seems awful, even assuming it would work.

So, upgrading Elyn’s machine to Linux (if it is even possible)
wouldn’t help. The lack of TurboTax would also be a problem — they
have an online version but, from what I’ve read, it isn’t as
featureful. The Linux worlds needs to make inroads with ISVs in order
to get users like Elyn; I really couldn’t recommend Linux to her
today.

At this point it looks like buying a new machine is the only
answer. I hate computers.