When I was 18, I wanted an Amiga to watch oldskool demos and play some games and modules (ProTracker). Then I got another Amiga 1200 (new old-stock from Amigakit!). Then I got 2x Apollo 040 that I sent to Cosmos for upgrade to 060. The other one didn't work and got fried, the second one worked when it wanted to. Both of them are totally smashed now.
Later I got an A600 + A603, and A500... Then I got an Amiga 2000! Oh my! Then Blizzard 2060 and Picasso II.
Result? A lot of money spent!
I regret everything Amiga I bought except for the Amiga 2000 and the "new old-stock" A1200. I really, really love the not-in-keyboard Amigas. I'll definitely buy an Amiga 4000 in the future.
EDIT: I've also wasted buttload of money on broken XBOX 360s, but finally I got one that I managed to JTAG.