Looks like 1.5 server is buggy. I'm trying it locally to evaluate before upgrading the server. First bug I've encountered is that achievements just plain don't work. Worse, because they don't work, I have this "helpful" popup on the top-right of the screen all of the time.
Oh, notch...
edit: Oh, according to the wiki:
Quote:
New Bugs:
Achievements only work in SMP if you have already completed first achievement in Single Player
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Off to try... and it works. Weird achievement system, too. You can't get any advanced achievements until you go and do the basic ones.