Well, I wasn't really looking for an Amiga, it sorta stumbled into my life. I was at a yard sale and saw it for sale, asked how much it was, the guy replied $40CDN, and I said, "Sure", without even thinking what I was getting myself into.
The fact that my A500 has a 68030 @ 40 Mhz, makes it worthwile for me to invest $$$ into it. I won't be investing that much, because there isn't much left to do anyways.
I saw a A500 + GVP530 combo last week on Ebay selling for $150US or so, which brings me to my next point. Why am I not upgrading my A2000? Well, it's NEARLY impossible to buy anything off of Ebay. I've tried bidding on a few systems, and they go for MUCH more than I am willing to pay... I don't see myself spending hundreds of dollars for a computer which I am unfamiliar with.
I'm taking this A500 as far as I can, and if I like what I see, I will continue moving onwards...