What is the difficulty level for migrating from windows to linux with plex?

Am I able to backup my DB and xfer that into the install as long as the HDDs are all labeled the same?Currently on windows everything is automated as far as content being added, HDD maintenance, system maintenance, and overall system monitoring.

Any and all input is appreciated.

Thank you, I am going to be implementing this soon. I just have to make sure my automation software will work for populating my server once its all transferred over.