I bought a brand new A600 with 40Mb HD. First I bought a joystick. Not that long after I got a second joystick and an external diskdrive and soon after that I bought a memory upgrade to 2Mb Chip for it aswell.
Next I got an A1200 second hand with a modem and a printer and it's first uppgrade was a PCMCIA CDRom. That was followed up by an order of a Blizzard1230 Rev3 with 8Mb memory and a 200W PSU specialy made for Amiga. I had to sit with that for a while and be happy, but HD space became a problem (120Mb isn't much even if it seemed like that compared to the 40Mb on the A600) and so I bought the biggest HD I could buy for money witch was a Quantum Fireball 3.2Gb drive for about 500$ (I belive the 4.3Gb HD was advertised the month after my purchase or something but still 3.2Gb would be the last HD purchase I would need... I thought at the time... most PC's I came by didn't even break the 1Gb back then). In the mix of all this my 28" TV died and I bought a very expencive Panasonic 14" monitor with Scart connector so I could get better picture... little did I know a decent Amiga monitor would've cost less and would've produced a better picture.