I expect a variety of opinions on this topic will get posted...but here in southwestern Va, even last year, I cut hay in mid December and it was some of the most beautiful I've ever seen. The thing about late season here is that it often gets rained on, but it doesn't seem to hurt it because the temps and I guess humidity are so low. In fact, if freezing temps hit the cut hay during nights, I've baled hay that was really a nice rich green color, but totally dry--sort of freeze dried.
In fact, I'm only about 1/2 way through second cutting now because the spring and summer rains (and breakdowns!) have set me back so far this year. But, there is a really good late hay crop because of the ample water. So, as we get further into fall, I'll often cut a field, and not even worry about it for a couple of weeks--rain or not, snow, whatever--and then when a few nice days hit I'll get it baled. Also, most of the winds we get are this time of year, which helps to cure the hay which is a bonus we don't see in summer. Seems like hay just can't go bad or mold this time of year, so it is almost easier haymaking in a way. The horse hay customers love the late hay, too, and ask for it. You do get a fair amount of leaves into the bales that are falling off the trees and blow into the field, but it hasn't been a problem for me.
Your neighbors might look at you funny raking hay the week before Christmas, but the quality and additional hay in the barn is well worth it in my opinion.
