I would say it's highly likely based off everything you've shared. Safe bet is to plan as if you will get it, and pivot later if you manage to slip by unscathed. Otherwise you risk having to disrupt your plans mid-flight.
If asked about your travel history, I would be more delicate than you are being here. An officer may be off-put by your tone around career success enabling extensive travel and the inability of Government employees to relate.
Attorneys have different theories. Mine is of the opinion that Montreal was always one of the most inefficient consulates in the world, and covid made it worse by accelerating an already substantial backlog of clients waiting for interviews and visa processing. The DS-5535 is a useful tool in this regard in that it removes mandatory processing timelines. This essentially gives the consulate the power to kick the ball down the road for a certain percentage of clients, reducing the immediate bottleneck. He thinks they're essentially misusing it beyond its original scope.
There has been plenty of "actual" evidence shared in prior iterations of this thread, so those would be good places to start. In particular, I seem to remember a stat that ~40% of Montreal Applicants are put through some degree of AP compared to the global consulate average of ~15%. My numbers / interpretation of this data point may be off, so someone please correct me if I'm wrong.