My first amiga was an A500 during 1991 or so following my Commodore 64. I used it with two floppies and 1MB of ram for about a year, and then picked up a GVP 80MB with 2MB of ram. I ran a BBS on it for awhile (CNET) until the 1200's came out and dropped a bit in price. Then I sold the A500 (I think) and bought an A1200 with an additional MB of fastram. Eventually I added an Apollo 1230 and 4mb of ram, for a total of 6.
In the late nineties I sold it in favor of a 486 laptop and started working professionally as a software developer.
Since then I occasionally get nostaligic and buy a bunch of Amiga stuff. Last year I found an A3000 and 1084s for $15 in a pawn shop. Later I picked up two more A500s with harddrives and ram for another 50 bucks.
I sold it all on ebay....
Recently I picked up another A3000 and after receiving it I have to admit I'm questioning whether I really wanted another classic Amiga... I think I might just hold on to it this time and save myself the trouble next time I get nostalgic.
In the future I'll be running AROS. At this point I'm desperately awaiting a TCP stack and ethernet support... when that happens I'll be installing it on my laptop (dual boot) and contributing in development. In my opinion tying the AmigaOS to expensive, proprietary, or non-standard hardware (A1, OS4, Pegasos) is putting one foot in the grave. Lets not go through this mess again. I think we've learned our lesson a few times already. AROS will be exactly what I want... a lightweight, fast, simple, clean, and customizable Amiga based OS which runs on common (inexpensive) hardware. If it'll run Amiga software (whether recompiled or emulated) that's even better.
-tom