It's a good idea to have plans, but having gone through this just recently with my father in law, don't list anything as a "collection" in a will. You can have separate instructions for an estate trustee that you trust them to follow (X gets my pins, Y gets the car etc), but once it's in the will, it can make things more complicated for them with respect to probate, and any other legal stuff that comes up. It does take some resourcefulness on the part of a trustee, but worst case some of the auction houses that deal with contents will be able to deal with a few pinball machines. Best case is someone looks for pinball collectors in the area, and finds this website, TOPL, Maple Pinball, or any of the Ontario pinball facebook groups, or they look for listings on ebay for an idea on value. I've done that for a bunch of classes of things from an estate recently, and have had some good luck with other collectors looking to pick things up in bulk. I've also pieced out other collections to try to get more value out of them. At a certain point with an estate, it's the trustee's call as to how much time they want to put in, or if they're at "just make it go away".
From my recent experience with this though, 4 pinball machines is easy. Only 4 things after all. Lots of small stuff are harder. Speaking of which, anyone know someone who buys high end knife collections? I've still got several hundred to get rid of
