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You could reach out and ask about future movement expectations or historical trends for the school, but I would NOT phrase it like you are insinuating you will. Don’t ask if you should be making other plans, you want to continue to portray yourself as a qualified and excited candidate who is interested in attending. Asking if you should be doing something else does not portray this.

EDIT: agree doing nothing is probably best.
 
I was hoping they have a rough idea by mid-May of who's getting off the waitlist and how many spots are left. So I hope they could say something like "we have mostly fulfilled our class" or "we expect a lot of future movement."

it would be a waste of time to reach out for that. By May, all initial offers of acceptance will have gone out. Schools will be moving folks from the waitlist as slots become available - not because they are sitting on open slots. The challenge is a space opens up at school A, causing a student previously accepted to school B to open up, which impacts school C, et cetera. In this instance it’s better to do nothing.
 
Frankly, you won't get the truth out of them. They will string you along because they want you as an insurance policy against an empty seat at the end of the cycle and they don't want you to drop off the waitlist in a fit of pique.

Keep preparing for another application cycle but don't feel you need to apply in two consecutive cycles. Some, including the very experienced @gonnif say that you should skip a cycle.
 
I'm on the WL at a bunch of places. Around mid-May, would it be alright to reach out to a med school dean to ask if I should be making other plans (i.e. that there is little chance of getting off the WL)?
Waste of your time and theirs.

BTW, you are rejected until you get that accept email, and so you should be working on Plan B right now.
 
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