That all sounds a bit odd... could you please share your server.log.zip
with me? You'd find it in Settings/Information.

There are various issues related to what seems lack of write permissions. Is the following folder and its sub folders writable for LMS?

/Users/{yourusername here}/Library/Caches/Squeezebox/

There are errors related the "InstalledPlugins" sub-folder as well as "updates".
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