Good question. I don't think there's a cut-and dried answer, though. I agree that while following the official deadline might add to realism, it takes a bit of the fun out of the stretch drive. In single season leagues, there usually isn't that much of a need for a deadline of any kind, but keeper leagues are trickier. Sometime around the end of August is usually a decent solution in order to avoid salary dumping of the kind that can badly hurt a league, but an earlier deadline might be a good idea for leagues where such veteran-for-prospect deals are very common.
In my own keeper league, we use September 1, which is just about the latest date where a deadline still makes sense.
Last edited by Arlo on Sat Aug 10, 2002 6:49 am, edited 1 time in total.