there are some albums - Beggars and LIB, for example - that i almost never think of putting on in the daylight. hm, no wonder i like it when the nights start getting longer. :E
Maybe not so much season commited but i do have a certain daily habbit. In the morning i play a lot of early sixties stuff (the Brian albums, Black box and the BBC sessions), during the day i play a lot of Handsome girls and recent bootlegs ('89-present) and when it gets late in the night i listen to '72/'73 boots.
Great question...I agree that I prefer them at times that correspond to their original release dates...except for live ones which, to me, sound best when they correspond to the tour dates.