Hmm, thanks for the thoughts.
Unfortunately, I can't even find an N64 emulator that works, so *shrug* but I'm not sure I see why it would be any more weird than Sega games or anything else with a PS2 controller. Either way, the DualShock has no less buttons or anything than the N64 controller so I'm curious if you could elaborate exactly what's weird about it.
As for 2 player in front of a PC being uncomfortable....point taken and something I hadn't considered. Like I said, it's not something that I'll be doing too often at all really, just something to consider when making the buying decision. I do have a 19in monitor though so I figure if need be we can always sit back away from the monitor