I started with a VIC-20 back in 1981, then quickly progressed to a C-64. I remember comparing the C-64 to a friend's new $5000 PC-XT. The PC was so far behind, it was laughable!
My first Amiga came in 1988, an A500 (I had been drooling over the A1000 ever since I first heard of it, but was never able to afford it). I later purchased a "Spirit Inboard" 1.5MB RAM expansion for about $1,500.
My second A500 was in 1990, it was a rev 6, with the 1MB Agnes chip. The old 500 was sold. I also purchased an A590 for it.
In 1992 I purchased an A2000. I hacked it to take my A590 temporarily until I could afford a proper SCSI card for it. A few weeks later I purchased a GVP-series II with 105MB Quantum and 2MB Fast Ram for $1,700!!!! Over the next couple of years I added a VXL-30 accelerator, more RAM, Retina II graphics card.....
Just before Commodore died in 1994, I got my A4000, and use it to this day as my primary computer (despite numerous attempts to jump ship to the PC). The A4000 has now been heavily expanded, Micronik tower case and Zorro expander, Cyberstorm PPC, Cybervision PPC, and numerous other expansion cards.
Last year I purchased an Amiga One, and am still awaiting OS4. (Why is it Australia is always LAST in getting Amiga stuff!!)
Incidentally, a couple of years ago I purchased an Athlon XP1800 system for running Amithlon and Windows XP. I was never able to get windows to work to my satisfaction (I refuse to wait 5 mins for a system to boot!), so I dismembered the PC and used the case and other accessories for my Amiga One.
Over the years, I have also accumulated other Amigas, such as more A500s, 1200s, another 2000, an A3000, CD32....
David