I'd go with the dual boot option personally. If you wanna get dirty, no sense just walking on mud, You need to roll around in it. That is how I learned linux, and it really payed off.
Some tips for an anime geek such as yourself:
For video, use mplayer (or mplayer with a frontend like smplayer). The stock version in ubuntu is an old one. You'll wanna get a newer svn copy as it has better ssa/ass support along with improvements to its built in ffmpeg to speed up h264 video watching.
Also, if you have an Nvidia GPU along with the right chipset. You'll wanna know how to work with vdpau in mplayer. Vdpau basicly means you can watch your 1080p h264 rips with only 2%~ cpu.
http://en.wikipedia.org/wiki/VDPAU <-- a list of supported cards among other things.
for an ubuntu repository with need packages:
https://launchpad.net/~nvidia-vdpau/+archive/ppaYou'll also wanna set this up (first):
https://help.ubuntu.com/community/MedibuntuIf you need any help with linux, feel free to PM me here on the forums or message me on rizon/irc. My nick on rizon is dankles too.
I'm one of those crazy fanboys, so I really dont mind helping at all. It helps my e-peen.

EDIT:
Oh yeah, don't use framedropping in mplayer when you play h264 stuff, because it has a weird effect. If ur system is slow, there are better config options to speed things up. Let me know and i can help you with that too if needed.
I only mention the framedropping thing because it seems to be turned on by default in smplayer and gnome-mplayer.