Xhonzi, you and I are a lot alike. I also tend to stay a generation behind to save money. I also stopped gaming when I finished school and got married, and later had my interest re sparked (thanks to a hand-me-down PS2 from a friend) and eventually bought a 360.
The DS with homebrew really is worthwhile, it is a lot of fun being able to play oldies like Monky Island and Doom on a device that fits in your pocket. As for Nanner mentioning its lack in ability to play regular Gameboy and GB Color games, you can just emulate those two. Just find a ROM for all the GB and GBC games you own and grab an emulator called lameboy. With the R4 they play flawlessly on the DS.
Xhonzi, since it sounds like you like Halo, do you have Halo 3 or ODST? We could co-op sometime.