Neil,
Unless you have a tiny iTunes library this just isn't going to work at
present.
My rescan (10,000 tracks) takes 20 minutes so expecting updates every 5
minutes seems a little optimistic!
I gave up on regular updates to the library a long time ago, and now
live with a daily scheduled rescan while I'm asleep.
There is a bug (1469) open on this issue if you want to add your
thoughts.

I also dont believe you'll be able to update a playlist that is being
played. 
If you select an iTunes playlist for playback, you're actually playing a
copy of it so it will be unaffected by any rescan changes.

Faced with these constraints I wrote a plugin that plays from iTunes
party shuffle, allowing you to access a smart playlist almost
dynamically (at one remove). 
It only supports Windows but I may be able to get it to work on the Mac
if Mac users (such as yourself) are interested in testing it!
www.jamescraig.co.uk/SlimServer


James
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