Take this for what it's worth, as I don't have a dory nor have I ever seen one in person, but, from a boat safety point of view...

    Try it, in shallow water first, where you can stand up if need be and walk back to shore.  Try it one handed too, to see if you can do it with a beer still in hand.  Try it after a few beers, if you think that might be something you do while floating next to your boat.

    Most boats you can re-enter from the water, although they range in difficulty from nearly impossible (a whitewater canoe) to super easy (that big power boat with a swim deck).  In general, you enter the boat over the stern (the bow sometimes works, you don't enter over the side or you'll swamp the boat).  A step might help make the entire process a little more "graceful".

    This will inevitably be easier if there's somebody already in the boat who can counter-weight it for you (not actually offer a hand and help you in, but actually sit at the opposite end of the boat to help balance the weight while you climb in all by yourself).

    But really, try it first, in shallow water.

Agreed,  Except for board sailors and catamarans,  I agree most small sailboats are nearly impossible to board from deep water, thus I'm wondering if anyone has ever boarded a CLC dory from deep water, assuming possession of a web-step up device..