One structural point that changes how you should pack regardless of how the conversation goes.
Even with the best preparation, there will be a flight where the aircraft is small and the bag genuinely cannot come aboard. So the goal should not be "this bag never leaves me" — it should be "nothing irreplaceable is ever in a bag that could leave me".
In practice that means a second, smaller pouch that is unambiguously personal-item sized and holds the medication itself plus anything you would need in the next day. That pouch never gets checked because it fits under a seat on any aircraft flying. The larger bag can then hold the bulkier equipment and you can afford to lose the argument about it.
Splitting the risk is more reliable than winning every negotiation, and it means the one time you meet an inflexible crew member is not the time it matters.