Again, thanks for the responses, you guys have given me tons of good advice and opinions.
The Bass Buddy looks awesome and I'd love to have one but its a bit outside my price range right now.
I'm still considering the Cafe Walter, but I noticed that their website provides schematics and I'm questioning whether building one would be feasible or not. I consulted a DIY stompbox forum and someone told me it would be doable while a friend of mine told me it would be a bitch and a half. Regardless, I'm pretty interested in doing it as a learning project. If anyone has any advice or knowledge on the matter I would appreciate it. Particularly if you know where I might find an already completed H1-A1 circuit board for the I could print up. Also sites where I could order all the components (which I'm not exactly sure entails) would be helpful, so far I've only got a soldering station and desoldering.
Right now I'm about to pull the trigger on a Line 6 Studio GX, which I wanted a a few years ago after hearing some things on youtube.
As for cans...
I'm liking the Sony MDR-700DJs for their price and cause they look frickin sweet, but I also read that they're not so good for jazz, which I am partial to. I probably should have mentioned that I'm probably going to using them mostly for playing and listening to jazz, funk, and classic rock.
Oh and the house I'm living in has tons of other musicians as well as a bass amp I'm free to borrow, I just prefer to practice through headphones.