My first was an Amiga 500 bought in 1991 with a 1084sd2 monitor and a tv converter for 720€ :_)
It had problems of stability so after some months of problems and going back to the shop the changed it for a new A500...
It worked flawlessly for years... I bought a 512kb ram expansion (I noticed it in the music of titus the fox and because I could load The One's Darkseed demo). I used it for DeluxePaint, DeluxeVideo (yeah, I know it was crap but it was fun anyway) and games (After the War, AMC, Budokan, Prehistorik, Quadrel, ShermanM4, Titus the Fox, etc...)
I moved to another city. My A500 died 5 years later with the disk drive. I sent it to repair and they gave me an A500+ motherboard with the old chips but the Fattest Agnus. I saw lots of mags and started to buy The One, CU Amiga, Amiga World, Amiga Format, Amiga Computing... I didn't know any Amiga user yet (Spanish mags had died and the only ones alive weren't available neither known in my city). I bought AUI and saw that the disks required KS2.0... I kept the disks some months and upgraded to ks2.05 (3.1 was very expensive). WOW! ks2.0 was great! disks loaded faster, I felt a lot of control, I started to use the workbench more and more...
After 6 years with an Amiga 500 I found an Amiga user in the city (oh, it was amazing! an amiga user!). He had an A500 with 1.3... I saw clearly that he wouldn't upgrade (money problems). I think that having been able to use ks2.0 was an important factor that caused me to continue using miggys.
Then I moved to Zaragoza, found AmigaInfo (an spanish mag), subscribed to it and I sent a letter where I asked if there was any local user group/club, and in the second number I bought my letter was published. In the third number Zurt (now one of my best friends) replied my letter... I was lucky because CUAZ have been founded just 2 months before or so. I meet the CUAZ crew and it save my "Amiga" life :-)
It's a pity that we don't meet so often... I miss the old times.