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1. Autumn and Summer I like. Winter I don't like at all, and Spring is even worse. It hasn't ever seen as much use as the other three, probably for the same reason Fall hasn't.
May is okay for a middle name, I guess, kind of blah. April and June are very pretty. The others, I guess they can all be used as first names but that doesn't mean they should.
2. It's pretty common for people to be given month or season names that they weren't born in. I would kind of draw the line and say that if you're going for a themed combo, you should do that in the appropriate season/month. My cousin is Holly Noelle and she has a birthday right around Xmastime. Either of those names is completely unremarkable any time of the year, but together they scream Xmas. You wouldn't put your Xmas tree up in July.
3. I wouldn't bother trying to work a name out of a month or season just to have a name that references the season.