1) how much do you want to spend
2) exactly what do you want to do (is lots of simultaneous I/Os important for recording say a live drum kit)
as far as the software is concerned I think it is pretty much a matter of preference. I know a lot of people (including myself) who have been very happy with Sonar however by the time you have bought a bunch of plugins it can get very $$.
As far as an I/O goes, what sort of sound card do you have ?
Can it except S/PDIF ?
If all you want to do is record guitar what about a pod xt (which can act as a USB interface / sound card) ?
Another thing to look at might be a line6.com tone-port
It may well be that the sound card will do as far as an I/O device goes with out the need for a USB interface.
My instructors page and www.studiotrax.net for all things recording.
my toons Brought to you by Dr BadGAS
my toons Brought to you by Dr BadGAS