Windows Media Server keeps crashing

I looked at the logs you attached. I could not see evidence of deadlock or an actual crash. The logs do show networking issues with your setup with DNS Rebinding protection affecting local network secure connections and they also show a Double NAT (probably you have 2 routers rather than a router in modem/bridge mode and an actual router)

Also I see you are switching from ethernet to wifi and the local IP address is changing when on wifi, which may cause issues for plex client apps connecting to your server

I would recommend sticking to either ethernet or wifi and using DHCP reservation to make sure the IP Address does not change.
Also if you are using two routers, have the ISP Router in Bridge / Modem mode so that you do not get a double nat

The logs were from 1.27.1.5916-6b0e31a64

After making the suggested changes for your network, update to the latest available public release 1.28.1.6104-788f82488 or latest 64-bit preview release Preview: Plex Media Server for Windows 64-bit version - Plex Media Server / Desktops & Laptops - Plex Forum and get me fresh logs if the issue persists. And let me know the IP Address of the device that is failing to access the server and the time when that happened