While I see your point, I don't think this makes sense historically. Dictionaries never supported such behavior before so you'd be introducing a new core concept to a dictionary. But moreover, you'd be changing the type of the value only on duplicated keys, and what about if you were to add another value of 2 to a? Are you making this a set, and why? I think it would come with too many caveats and assumptions in the PEP.

I'm not saying you have a bad idea/logic here, just that I'm not sure it's the best thing for the dict.