I have one of these, too, and it is pretty nice. The initial setup is actually really simple, but it has the ability to be much more advanced. It has worked flawlessly since initial turn-on. We then use several Unifi APs around the house.
I think that rather than trying yet another foam mattress that I end up not liking and thus replacing in a year, we are leaning toward a (bottom end) Hastens. It is a lot of preposterous marketing nonsense, but they are really comfy.
You can plug a 2TB HDD into a Rpi via USB, then connect the Rpi directly to the transporter/touch with a crossover cable. Run Squeezeserver (or whatever they call it these days) on the pi (and possibly a DHCP server to give the touch an IP) and you have exactly what you want with one small extra box. And it would be pretty easy to make a small box that would hold the pi + HDD to bring you back down to a Transporter with a box hanging off the back.
This strikes me as the right answer. Put it in a big box with a touch screen and use it directly, or use it as a server with a rpi or tablet as the player.
When I was little, we went on vacation in the Bahamas. There was a huge roach in the shower, so I picked up my brother's shoe and threw it at it. I missed, of course, but the roach ran right into the shoe to hide -- problem solved.