The Xbox controllers definitely suck for older stuff, so I picked up a pair of the Street Fighter Anniversary Edition controllers. For those not familiar, this is a "retro" gamepad layout, similar to that of the six button Genesis. Works fantastic. I do have some of the Xbox>PS2 converters as well, but they can be hit-and-miss like you mentioned.
As far as furniture, most of the necessities are taken care of, except for the seating. The thinking behind the Ikea sofa (as opposed to something nicer) is that the area just can't accommodate it. Most sofas aren't designed to go through the standard 30" door on a typical bedroom. In the past, I've had to resort to sofas I can carry in piece-by-piece. This makes something like the HomeReserve or Ikea sofas ideal, as they require assembly anyways. Most of the "nicer" sofas come preassembled as a single unit.
I will likely take Hatta's advice and just use S-Video for the time being and upgrade as I see fit. I've been trying to cover so many bases at once, I didn't stop to think that I can just use what I've already got and go from there. One thing at a time.
Well now that someones mentioned it I definitely won't, or if I do it'll be another character from that version of clue. I'm kinda partial to the stodgy old bastard though.