If you're looking for an external interface for a Windows machine, the only hard and fast rule is to make sure whatever interface you select is USB 2.0. Within the price range you mention, the quality of the converters are pretty similar, so look for a) features; b) drivers; c) latency.
In my research, the Roland Quad Capture is probably the top interface under $300 compatible with Windows (which I assume you use, considering you're on the Cake forum.) That said, it is limited to 2 analog in/out and it will not accommodate your two sets of speakers without an external mixer.
Another interesting choice, if you can stretch your budget by $50, is the M-Audio Fast Track Ultra. Said to be faster than the Roland unit, but with perhaps slightly worse pre-amps. This unit has a much more comprehensive selection of analog ins + outs.
These units, plus the Roland Octa and the RME Babyface (outside your stated price range,) are the ones I researched before my recent Octa purchase. Hope that gets you started.
post edited by Everything Flows - 2011/12/16 19:39:46