I started with a few P&S (a few Sonys and Canon)
First Canon was a P&S SD500.
Upgrade to Canon S2 IS.
Upgrade to 30D with kit lens in 2007. Bought 50 1.8 and Tamron 17-50 within 1 year.
Got a job doing weddings as a 2nd.
Got another body, 5Dmk2.
Sold 30D and bought 7D.
Between 2008 until now, sold the kit lenses (from 30D and 7D) and 50 1.8. Bought a bunch of other lenses, flashes, and accessories.
Just last December, with all the great prices on some of the lenses, Upgrade 70-200 to mk2 and bought 85 1.2
Can't wait for 5Dmk3, whenever it's coming out.