thinking of making a switch but cant decide.

So Currently I am an ubuntu User, have been for about a year or two.. my problem is I am also a power user as well and am starting to get bored with ubuntu and the whole "just works" manifestation.

My system consist of
3 SATA HDD
AMD64 X2 /wRadeon HD
with the first HDD Partitioned as 35GiB WinXP (I would ditch it but I use it for Media Apps, that sadly theres still no truly comparable ones on LINUX)
Second is 15Gib "/" partition and 45GiB /home

The other drives =650GiB FAT shared partitions- a GiB of /swap

I was thinking of Gentoo but read it was not great for Dual-Boot.

so I thought Debian Net-install might be a decent choice but I guess I am seeking advice.