I found this Database Repair Error: no such collation sequence: icu_root which states you cannot use the normal sqlite3 which goes against the instructions in their own article I posted above. So I went through those processes using that information but it did not seem to help – STILL CRASHING. Although it did remove the errors I got with the sqlite3.exe I tried originially. Here is that output.
C:\Program Files (x86)\Plex\Plex Media Server>copy "J:\PLEX\Plex Media Server\Plug-in Support\Databases\com.plexapp.plugins.library.db" "J:\PLEX\Plex Media Server\Plug-in Support\Databases\ORIG4"
1 file(s) copied.
C:\Program Files (x86)\Plex\Plex Media Server>"Plex SQLite.exe" "J:\PLEX\Plex Media Server\Plug-in Support\Databases\com.plexapp.plugins.library.db" "DROP index 'index_title_sort_naturalsort'"
C:\Program Files (x86)\Plex\Plex Media Server>"Plex SQLite.exe" "J:\PLEX\Plex Media Server\Plug-in Support\Databases\com.plexapp.plugins.library.db" "DELETE from schema_migrations where version='20180501000000'"
C:\Program Files (x86)\Plex\Plex Media Server>"Plex SQLite.exe" "J:\PLEX\Plex Media Server\Plug-in Support\Databases\com.plexapp.plugins.library.db" .dump > dumptest.sql
C:\Program Files (x86)\Plex\Plex Media Server>"Plex SQLite.exe" "J:\PLEX\Plex Media Server\Plug-in Support\Databases\com.plexapp.plugins.library.db" .dump > "J:\PLEX\Plex Media Server\Plug-in Support\Databases\dumptest.sql"
C:\Program Files (x86)\Plex\Plex Media Server>del "J:\PLEX\Plex Media Server\Plug-in Support\Databases\com.plexapp.plugins.library.db"
C:\Program Files (x86)\Plex\Plex Media Server>"Plex SQLite.exe" "J:\PLEX\Plex Media Server\Plug-in Support\Databases\com.plexapp.plugins.library.db" < "J:\PLEX\Plex Media Server\Plug-in Support\Databases\dumptest.sql"
C:\Program Files (x86)\Plex\Plex Media Server>"Plex SQLite.exe" "J:\PLEX\Plex Media Server\Plug-in Support\Databases\com.plexapp.plugins.library.db" "PRAGMA integrity_check"
ok
C:\Program Files (x86)\Plex\Plex Media Server>