Hi and welcome to the board.
First, would you mind adding your company's web address to your profile? On an issue like this the techs will be much more responsive if they know who they're talking to.
Next, I'm not sure I fully understand the issue. True Supervisory Monitoring will terminate when during the initiation, but by initating a remonitor a few seconds later, the supervisor is back monitoring the call. Is this an issue?
Also, is monitoring the trunk an option? If so there are some very good work arounds that will allow a supervisor to transfer to an extension off a SL Card.