Music randomly stops playing on both web and desktop players

Is your ISP xfinity? Xfinity XFi Security

Are both devices connected per wire and not per WiFi?
(Try at least to use wire for the “server” device.)

On windows, I recommend this setting (for both server and client)

Set your ‘Secure Connections’ server preference to ‘Preferred’, instead of ‘Required’.

Have you tried Plexamp?