I spent an hour going back and forth.
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I thought perhaps the USBridge sounded perhaps a little better than the NUC; a bit cleaner and tauter (bass). But I could also have imagined the difference; I wasn’t doing a true blind test. It certainly wasn’t night and day, if at all. Whereas when I went from Pi USB to USBridge, my wife commented on it straightaway (I got immediate approval to buy a 2nd unit :)). So on what is probably a USD5k set up, you could call the NUC high quality. If you were spending $50k of your customer’s money on a system, maybe you would want to try for yourself.
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NUC v. Pi – NUC clearly better (i.e. roughly on par with USBridge). Separation, imaging, bass response (I’ll stop there, before I sound like too much of a pretender).
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Transparent / auto updates – I installed Ubuntu server, and then Roon Bridge. Ubuntu server is rock solid, and Roon Bridge updates cleanly when Roon pushes updates. You could probably leave it in a corner and never have to touch it. That said, I am an Ubuntu tinkerer, not an IT professional – I would defer to others with more knowledge; you would be trading off security implications of not patching the OS v. risk of a bad update and it breaking.
Supplemental to system description provided in previous post – source material was either DSD64 or Tidal MQA, all upsampled to DSD128 by core. Listened to Miles Davis (So What), first few tracks from Daft Punk’s Tron soundtrack, and Mogwai (Remurdered).
Hope this is helpful.