Update Service Crashing

Did you change the LocalAppData path away from the default folder location?
If so, did you also change the registry key which is mentioned in the “Addendum” of this article [HowTo] An extended guide on how to move the Plex data folder on Windows to the same location? It should be.

Is your appdata folder on an encrypted drive? If so, set the startup mode of the update service to “delayed”.