Well, I had gotten my C=64 back when I was in grade school (mid 80's, sometime) and been quite happy with it. By Jr. High my friends and I all had one, and most had modems and we were pretty active in the local BBS scene. (When our moms weren't interrupting our hours long downloads by picking up the phone....)
Anyhow, one friend of mine whose family was richer than ours kept getting new machines every year or so. They had a C=+4 which we teased him endlessly about... Then a year later, got a C=128, which was actually pretty cool, but we still teased him because for everything except typing a paper or dialing a PC board you had to use C=64 mode for, anyhow... And, then, it must have been late 1988, he got an Amiga 1000.
We started teasing him again about jumping ship again on the C=64... Sure, Workbench was cool, and certainly a lot faster and more useful than GEOS, but where were the games? A few repackaged titles with nice graphics, but nothing that REALLY set it apart. (We were already getting a bit jealous, but not showing it, yet). Sure, Defender of the Crown looked stunning, but the C64 version was quite playable and on a fraction of the budget.
Then, the next year, he called us over and popped in a little game that just came out (Shadow of the Beast), this time we were forced to acknowledge he'd gotten the real upgrade. I'd never look at my C=64 quite the same way again.
A few months later I'd scraped together enough money to put together (along with selling all my C64 gear) to pick up an Amiga 500 and 501 card. Great machine. I never looked back. Over time I added a sidecar HD and RAM expansion, digitizer, and a few other odds and ends.
A few years later I sold off all the A500 specific gear, and traded up to an A1200 with the GVP'030. WICKED-FAST machine. I loved it. It started being plagued by the A1200 graphics corruption hardware bug thing, though...
So, of course, I sold it to get an A4000. At first, I was actually disappointed in my A4000. It wasn't much of an upgrade over the A1200. (Going from a 40mhz '030 to a 25mhz '040 didn't make much difference, at all.) So once again, I scraped and saved, and threw a Phase5 CyberStorm 060 in it. THAT was the way the 4000 should have shipped from C=. ROCKET SHIP fast. :-) A year or two after that, I added a new CV64/3d to it, as Commodore was going under. I swore I'd never sell that system until something honestly better came out. I still have it.
Of course, for work and junk, I was forced to go more and more toward PCs, and around 2000 or so, I bought my first Windows PC. (And truth be told, I'd been using a work PC laptop more and more even before taking that plunge.)
Sometime a couple years ago, the CyberStorm '060 died on my old A4000. It's sitting up in storage, awaiting me to get nostalgic enough to send it to Amiga Center France for a good overhaul. In the meantime, I have my PCs as main computers, and an A1200 GVP'030 (a lot like my old rig that I sold) that I enjoy as my retro machine. :-)