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I see what you mean. Basically the short cage I have will work with 34T or 36T but will be slack on small-small, which I wasn't seeing as an issue since I don't do that.
I think I'll get a 36T or 34T cassette and just see how close the jockey wheel is. If I can't adjust around it, I will get a Wolftooth.
Of course not, but that's the reason you would need a longer cage. A SS derailleur will probably be fine for any combo as long as you don't go to the extremes of cross-chaining, but I don't know how syncro shift works and it may drop down the front before going through the block etc., so not something I'd risk personally.