I think I fall into that category of "stuck in 1991" :lol:
My A1000 is very nice. I've installed the Rejuvinator, it's got a 2MB Agnus, Super Denise, Kickstart 2.05 or 3.1 onboard, or 1.3 through a floppy, and an extra 1.5MB inside. Outside I have a Dataflyer with a 540MB drive and 1.3, 2.04, and 3.1 each bootable in a different partition.
I have sitting unused a CSA Derringer 50 with 32MB ram, but I'm not sure if I should use it or not. I tried once, but I think I ran into compatibility issues with games, so I went back to the 68020 (no speed increase really). This was 10 years ago, and I didn't know much about Amigas, so I might not have installed the 68030 libraries at the time, or known of WHDload.
I think I might give the Derringer one more try, but my only use of the Amiga is mainly Deluxe Galaga, so I'm just not sure if it's worth it because the system works great as-is.
For any high-powered computing task and all day-to-day stuff I would use my dually PCs. If the Amiga was my only computer, I could see that it would be a great idea to upgrade it.