I upgraded a -stable box to -testing. Mostly went well, but in one or two cases ... well, not so well.
Random starting of daemons: Yes, this has been the case in Debian for a long time, however, it gets worse when a dependency pulls in a new daemon and restarts *that*, and suddenly you are left with a nice, blank page. Actually, it didn't do that, but gave you a directory listing of what it *thinks* is the root www directory. You're left wondering, why? (the culprit, by the way, is Apache2)
Stuff that does not work out of the box: I could not get Exim4 and mailman to play nicely. First: Exim4 does not handle pipe transport out of the box, so none of the aliases stuck into /etc/aliases for mailman actually work until you uncomment it out. Mailman does not play nicely because Exim starts with Debian-exim group, and mailman will whine because that's not what the default gid is configured to at compile-time. The README files does contain some information on how to make it work .... but it was more like "Oh, just enable some random crap in your configuration file to make it work" ... hmm, nice work, considering the popularity of mailman as a mailing list software and exim as a MTA.