I think you misunderstand, I was talking about moving to a completely different machine. It's drop-dead simple to do.
It's true that an iMac or mini are not very upgradeable internally, but that's more the form factor than anything else, and you can substitute newer bigger drives internally if you like. I have generally hung FireWire drives off them instead, but YMMV.
I've personally done at least twelve full version upgrades of MacOS, including one TiBook that had full version upgrades five times. I had one problem across all of them: That TiBook had a nine-letter password set back when it was new with 10.1, and became impossible to log into when upgraded to Leopard (10.5) because it had only one account. There was an upgrade bug where passwords of more than 8 characters that had been set with 10.1 would not carry through.
It took me about 45 minutes to work out how to fix that (the obvious approach using the boot disk got me an admin account, but I still had to reset the password on the old one, and that was mildly annoying). That is around seven hours less time than the minimum I have ever spent on a Windows upgrade, and considerably less time than I had to spend trying to figure out how to get Vista Home to talk to my NAS boxen (MS changed the minimum security requirements for network shares in Vista Home for some inexplicable reason).
I am more than a little dubious about the claim of a 1998-era PC running W7. That would likely max out at 512M unless it was exotic for the time (meaning server-class hardware), and W7 wouldn't install on something that small, and the CPU and graphics would not be anywhere near W7 minimums either. I got complaints installing it on what were pretty well configured 2005-era machines and they ran poorly even doing basic things until I put at least 2.5G RAM in them.
In contrast I had a 1998 era G3 clamshell Mac running Tiger (the last version that would install from a CD), and I had Leopard running on a 2001 TiBook and 12" G4 Powerbook. The funny thing to me as I advanced from 10.1 to 10.2 to 10.3 to 10.4 and finally 10.5 was that each upgrade actually ran better on the same hardwar than its predecessor *despite* having greater capabilities.
I have to compare that to Windows. XPSP2 doubled RAM requirements and Vista quadrupled XPSP2. Win7 didn't get much worse than Vista, but it is of course not much more than a service pack to Vista. I've never seen a version of Windows that ran better on the same hardware than the one before since WinNT 3.1->3.5.
Snow Leopard makes a big break in that they dropped support for non-Intel, which means that machines I bought expecting 6-year lifespans are only going to get 5 before I hand them off to someone else. In the world of Windows PCs I'm lucky to get much more than 2 years before I roll the machine down into the Linux server farm and get something that runs the latest Windows reasonably well.
YMMV, but in terms of longevity Apple has done very, very well in my experience. And in terms of ease of migration to new hardware, which is what I was talking about previously, they are second to none.