Well, once I had gotten the playback from Cakewalk up and running with Shoutcast, I ran into another problem. It seemed that as long as Shoutcast was active, I could play but not record any audio in Cakewalk.
The solution came to me before I came here to ask for help. I have two soundcards, an AWE 64 and a Darla 24. The digital audio gets recorded with the Darla 24, and the AWE 64 is strictly for MIDI. Thus, my AWE 64 card's audio features were not being used. So, I went into Settings/Control Panel/Multimedia and changed my prefered audio playback and record to my AWE 64. Now Shoutcast gets all its audio to broadcast from the AWE 64 card, leaving my Darla 24 open for both recording and playback. The outputs on the Darla 24 card are split by each channel, left and right, by 1/4 male to rca female connectors, and then a dual rca male to 1/8 male y cable, then a 1/8 coupler which is then plugged in with a 1/8 male to 2 1/8 female y-cable, which the 2 females send the audio out, 1 to my speakers, one to my AWE 64 line in, via a 1/8 male to 1/8 male cable.
So now I can hear the audio that I ma playing and recordingas well as have the same thing go to the AWE 64 for broadcasting. It's all in full effect now. =)