Which is best second week in May or last week in September?

Most of our trips have been in May or September the last 20+ years. Definitely prefer May, weather wise, by a mile. Late September is still basically full summer in Orlando. May can be hot but less humid and it at least cools down a bit at night.

Crowd wise September is generally better, but May isn't that much different, especially the first couple of weeks.
 
We were just there the second week of May and really enjoyed it. Yes the temps were still in the 90's but it was fairly breezy so it wasn't oppressive. The crowds were very manageable as well. I judged that by the booths at EPCOT. Very rarely did they have lines, even during the lunch hours. We usually go in June, which isn't TERRIBLE, but this was much better and I think we'll aim for this time of year from now on. It's a good "off week" right after spring break but right before the Memorial Day holiday.
 
Just returned from our first May trip (9-22nd). We usually go in late September because it’s our anniversary, including in 2023. I found crowds and heat similar but we loved May! It is an advantage not worrying about hurricanes (not at WDW but flight delays and changes. This has happened to us) or fighting crowds on non-party days. If you don’t care about MNSSHP, I would choose May.
 

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