I remember my 1st CD ROM drive. Had to travel to a town down the coast that had a brand new BestBuy store to buy it. Connected via the kit's included soundcard, & took a bit over a week to finally get everything working, playing with interrupts, memory settings etc. Remember emm386 with a small bit of loathing. Win95 had a lot less drudgery attached -- I was ecstatic. :)
98 & 98SE came & went. Never really got hands-on with ME. I wanted to, but it seemed like it was over before I had much of a chance. XP OTOH I remember as being pretty controversial -- it added roundness, what was called by many a Fisher Price interface. Why in the world waste precious resources on looks? PCs were to get stuff done, &/or for hard core gaming -- if we wanted something to look at we'd use Macs. ;)
XP also [at least eventually] made upgrading mandatory for hardware & software compatibility. I was expecting similar from Vista, & did quite a bit of work getting some XP hardware working there, but turned out I was wrong. My hardware & software continued to work not just OK, but better in XP. For me the experience was very much like 8/8.1 -- had the newer OS installed, but never found much reason to go there.
To me 10 today feels like win7 when the 1/2 way point was still ahead of it in Beta. I got my cheapie tablet with 10 in mind, but so far it's a shrunken desktop PC while I wait for the October update, so I can install store apps to the microSD card. I play with or in 10 from time to time, but the upgrade is so onerous with software installed, it feels like one or two more ISOs & I'll be ready to install my main copy of 10 fresh & finally start adding a bunch of software. I upgraded the copy of 8.1 I was ignoring so I can wait a bit longer.
You're right about USB -- probably right about dual monitors, but I've just never gotten into multi-monitor setups. I've tried it, can see how some people want or need the screen real estate, but wound up with the 2nd monitor turned off most days.