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In other words, is it worth it to reconfigure one's server to allow deep crawling of dynamic pages, or is a separate site map good enough?
SE's have always recommended developers to use site maps whether the sites are dynamic or not. Whether you reconfigure or not, create a sitemap and link to it from the home pages as well as other pages within.
On the reconfiguration part, I'd search around here for some more info. Similar questions have popped up on numerous occassions with other members laying out great answers.
Most use mod_rewrite, so you can change
your_page.htm?id=99
to
99.htm or /99/page.htm or abc/99.htm etc etc
as far as your db is concerned, it carries on as normal. You'd just have to add a few lines of code for the mod_rewrite and perhaps change all the URL's you use on your site to point to the new static pages and take advantage of the whole idea.
Highly recommend checking out some of the old mod_rewrite threads for solutions....