I know what you mean, on both scores. Have to tell you though, that I would have NO trouble ditching Win 98! I refurbed an old HP, a few years ago, and used its Re-Install disk... which turned out to be Win ME, about the same thing. I gave that one away faster than you can say BSOD!
Yeah totally understand that one. The annoying thing about W8 is how difficult M$ have made everything for desktop users. Such as a simple thing like booting into safe mode with F8 where you need to do a BCDEdit or use a third party app. It seems to be an endless litany of work-arounds and third party software to get it back to the efficiency of operation that existed in Win7.
In general terms PCs have only ever really been a hobby for me, aside from the actual work jobs I do on them like spread sheets for tax work, banking, music and movie editing, etc. I have no formal education in PCs aside from a few odd units from yesteryear when doing Electronic Engineering; and they're all prehistoric now. By no means do I have an in-depth, comprehensive range of knowledge.
I really only did things that needed to be done to make the PC work the way I wanted it to work; unless something got my attention and became a challenge or a curiosity. What I do know I know well, but there are a lot of gaps. And I could never get into it again like formal tertiary study, which would take all the fun out of it. All the repair work I've done for others was really to satisfy my own learning and interests. So they benefitted and so did I.
And sometimes I hope I'm not putting other person's data at risk. I recently fixed a late model Dell desktop with RAID setup for a friend. It wouldn't boot up. And after a lot of work with no joy was on the point of reloading, albeit losing his data. Then purely by chance when rummaging through the BIOS I discovered the disk config was AHCI instead of RAID. Changed it back and hey presto, all good! A month later without him doing anything, it changed back to AHCI. Still haven't worked that one out short of spooks, but this time it only took 2 minutes to fix.
Over the years I've repaired countless PCs pro bona for friends and acquaintances, especially after I retired. And the thing that never ceases to amaze me is why people don't back up their data to external media. It's so easy now with external HDs, flash drives, DVDs, cloud. Then when their PC crashes they fly into a panic at losing their data. One woman had something like 7,000 emails saved, and Outlook Express couldn't delete because the storage deletion temp was over the limit. There was a work around, but I mean, 7,000 emails already!!! And that was the scenario of my friend with the Dell.
