OK, something happened and I lost my long well thought out answer. So here's the gist of it.
100' using serial and baseband audio isn't going to work. At best standard RS-232 levels will run about 25' or so reliably. Unbalanced audio will likely pick up a lot of noise/hum, and you'll likely need a distribution amp. Not impossible, but there's a much simpler way.
Ethernet will run 100 feet easily. WiFi with directional antennas should have no problems with that distance either, but you'll need a fairly clean path (no leaves or other objects). It would require some configuration effort, but you could use a Raspberry Pi connected to the CAT interface and a USB sound card (the internal sound on a Raspberry Pi is output only) to do what you want.
To get the audio you would run a program called IceCast. This would allow you to stream audio across your home network to any device that can pick up Internet audio, as long as you can manually enter stream data:
https://stmllr.net/blog/live-mp3-streaming-from-audio-in-with-darkice-and-icecast2-on-raspberry-pi/The CAT control gets a little more involved. The easiest way would be to use a utility program called ser2net:
http://lesser-evil.com/2013/04/raspberry-pi-ser2net-cheap-nm16a-serial-console-server/However, on the remote end you'd need a program that can use a TCP/IP control. I'm not certain but I think the Kenwood remote software is capable of this, I'll let others who are more familiar with Kenwood's remote programs to chime in.
Another method would be to run Hamlib on the Raspberry Pi. Hamlib can create a "server" for your radio that other programs can connect to. Not all features would be available, but it is fairly standard:
https://sourceforge.net/projects/hamlib/you could then run a program like FLDIGI on your end PC for rig control. Fairly overkill but will allow you to change modes, freqs. and other basics:
http://www.w1hkj.com/FldigiHelp-3.21/html/rig_control_page.htmlAlso just came across this page that shows how the author uses a Raspberry pi to remote control his Elecraft K2:
http://alloutput.com/amateur-radio/remote-transceiver-operation/network-transceiver-setup-notes/