„Come and go“ problems are not easy to solve.
here are my thoughts about your problem.
a. I’m wondering what happens if you play music-playlist „forever“ from a USB disk. Not network streaming. Does it hang the server?
b. You are writing that you wife looses some elements in the app-Menu. Maybe there is some Network related „hickups“ on your LMS-erver or your LAN/WAN, since your LMS-server are loosing some menu ingredients from your http://www.mysqueezebox.com account.
((c. Maybe, You could try upgrading your SqueezeLite player to latest Max2Play version: Squeezelite Max2Play v1.0.3 based on v1.8.7-999))
I also get problems when I change name with „space“ in name. Seems like the the Squeezelite and Multisqeeze dont like split names. I just uninstalled and reinstalled the Sqeeze. No problem now.