I started with an Amstrad PCW, whic I bought 2nd hand. Then I bought a new 486-sx something or other from an electrical retailer that was going bust. It was cheap and ran Win 3.1. It was a waste of time and money but whetted my appetite for computers.
Currently I have a bespoke AMD box (bespoke in the sense that I built it myself and it was cheap
) , a server which was given to me by a builder (a nice Compaq Presario 5420), a HP Omnibook XE3 bought for me by my employer and a Toshiba Satellite 220CS (p133 48mb - my current box of choice because it's soooooo solid. And it's got Debian on it!!!) that I have brought back from the dead. I didn't pay for this one. I also have the makings of another box (AMD-k2) in various drawers and boxes around the house.
I am currently trying not to buy a Thinkpad T21 because I'm not sure if £299 is a good price.