When i was 20ish, i bought a Kyocera S4 iirc, to take photos of things to sell on eBay or QXL. Then in 2000ish I attended my first British F1 GP, i got some really bad photos from the grandstand, the year after i again attended but took a MiniDV camcorder and shot some really bad video footage...
From these 2 years i decided i enjoyed taking photos and video wasnt fun to shoot, so i decided to upgrade my poxy old Kyocera compact... this took the form of saving January-June to buy an new piece of kit to take to the July F1 Event.
This has continued year on year to form the following pattern.
2003 = Canon IXUS V3 Digital
2004 = Canon 300D + Canon EF75-300
2005 = Canon 300D + Canon EF75-300 / Canon 20D + EF100-400L
2006 = Canon 20D + EF100-400L / Canon 1dmkII + EF300f2.8IS
2007 = Canon 1dmkII + EF300f2.8IS +1.4xTC / Canon 5D + EF70-200f2.8IS
This year im taking
2008 = Canon 1dmkII + EF300f2.8IS +1.4xTC / Canon 1dmkII + EF70-200f2.8IS
And next year im hoping to be taking, unless of course Canon finally either fix or discountinue the 1dmkIII and release a 1dmkIV which i may be forced to upgrade too.
2009? = Canon 1dmkII + EF400f2.8IS / Canon 1dmkII + EF500f4IS +1.4xTC