Mine went something like this:
2004 - Sony Cybershot P&S
2008 - 400D + kit lens
2009 - 50mm f/1.4
2010 - Branched out into film with a Leica M4-P & a few lenses + a Canon EOS 3
Next will probably be either the 24L or 35L, then the 135L, then I should be done for a long time (in theory) ...