Is the Squeezebox Touch complicated?

It does work, but like all computer audio, it can be fiddly, not as easy as just popping in a silver disc and hitting the play button.
It doesn't do anything that can't be done in other ways. Mainly it provides a nice GUI to access music from various devices. After learning how to use it, I mainly use it for Internet Radio.
Before buying, ask yourself what you want it to do. Then ask what are the
Alternatives, and we can discuss the pros and cons of each.

I have a duet and find it to be very easy to deal with.
If you can connect to a wireless network in windows, you can deal with a S/Box no problem.
The few times I have personally seen issues, it has been someone trying to upload or download files while using their drives as the server...or the kids flooding the home network playing games while trying to play music...or not knowing that they cannot have the PC power management shut the drives off and expect instant response when they fire the S/Box up.

I have had to reboot mine a few times, but compared to the ease of having everything at the touch of a button...it has been a true joy.
I could not be happier and the sound, using a DAC, is awesome. I run FLACS mostly and try not to ever touch mp3.

Love my SBT, and have yet to have a dropout. I paired it with a VortexBox Appliance (~$400), all connected to my home wifi network. I love the sound through my K-Works SuperBerry DAC. Every bit as good as playback from a CDP.

I am ripping many homemade CD-Rs of vinyl and other things that don't get any metadata. Using MP3tag, I edit all the tags by hand. A real PITA, but I need only do it once, and as Mapman said, GET BACKUP! I already had to restore from my backup when a Vortexbox upgrade went wrong and I had to do a clean install. Restoring from the backup worked like a charm! Besides, my CD-Rs of vinyl sound way better than Red Book CDs of the same recordings.

Squeezebox Touch = entry-level digital audiophilia for "dummies" (actually, smarties) :-P

"Squeezebox Touch = entry-level digital audiophilia"

That's a good thing.

Simply add the right external DAC to meet your sound expectations and no longer entry level in performance IMHO, rather, already a serious contender for most audio hounds.