I started out in 1987 with an Amiga 500. I purchased a 512K trapdoor memory expansion, extra floppy drive, and 1084 monitor.
About a year later I sold the A500 and bought a used A2000 system. To that I added a SCSI card, Commodore 020 card, Microway flicker fixer, and a Mitsubishi diamond scan monitor (able to to 15.5Khz and 31Khz).
In 1990 I sold off the A2000 system and purchased an A3000 16Mhz system. I knew I would upgrade the CPU at some point so I didn't want to spend the extra for the 25Mhz version. I eventually added a progressive peripheral Mercury 040 card, and a couple GVP high speed serial cards. Oh.. And I had to buy a used A500 since none on my games worked on the A3000

Once the AGA machines came out I game up. In five years I had spent over 10K on my computer hobby. I wasn't going to fork out another couple grand for an A4000 that was in some ways inferior to my A3000.
About a month before Commodore went bankrupt (1994) I sold off my A3000 system (kept the A500 for games), and I built myself an IBM Pentium P5 60Mhz computer with the money.
I still remember that PC well. 16MB RAM, Orchid Celsius VLB graphics card w/2mb VRAM, Sound Blaster Audio, CDROM, IDE VLB Controller with high speed serial UARTS, Western Digital Caviar HD. It's sad.. But I knew at that point I had made the right decision. That PC lasted me for four years until I built a Pentium II-233 system.
I still have a soft spot for the Amiga. I currently has 2 A2000's and an A500.