This appears to be a QuickFIX/J quirk (some might consider it a bug). If ResetOnLogon=N then no ResetSeqNumFlag=Y is sent when the session start time triggers a logon. If ResetOnLogon=Y, the ResetSeqNumFlag=Y is sent on every logon. I believe this is not a big problem in practice because participants in a FIX session typically reset their sequence numbers locally after a session ends (logically ends at the end time, not a connection disconnect).
If you want to slightly modify the source code to implement this behavior, you'd modify the quickfix.Session next() method. You could add a local flag that indicates a session has restarted (per the schedule as determined by checkSessionTime()). Pass that flag to generateLogon() and that method would use it to determine when to send ResetSeqNumFlag=Y regardless of the ResetOnLogon configuration.