If any of his gear has CAT interfaces, a simple solution would be to use a PC with a CAT cable and the audio running to a soundcard. Flrig allows for remote control over the network and voice can be passed to the remote PC. He can do digital, voice, and CW all from the comfort of his bed with a laptop and headset. If he only has really old fully analog gear, this won't work and he'd be better off using KiwiSDR or buying him a "shack-in-a-box" type unit that would let him do anything from HF to UHF with his existing antenna and coax lines.

http://www.w1hkj.com/W3YJ/Remote_Article.pdf

But you can use whatever old PC you can dig up rather than a raspberry pi.