Thinking of switching to a convertible before next summer, prob dealer stock so presumably best time to do this will be in the middle of winter if not before when soft top demand/prices weaken ?
Just do it now and enjoy the last few weeks of warm summer. The prices may dip a small amount but so does good stock. Buy now while you have a decent choice.
We discovered the joys of open top motoring in a Mustang in California 9 years ago, alway wanted a convertible since then. Got a Boxster GTS 3 years ago and would be lost without it (in the summer at least lol). Go for it, it's not winter yet, even if it seems like it oop North.