Check out the Lightbox Matrix page, which has a nifty menu that allows you to specify the features you're looking for and tells you which lightbox supports your requirements:
The Lightbox Clones Matrix « planetOzh
I think it's OK if you only have a few pages/sub pages, but more than about ten and I agree this would probably become unmanageable. At that point you should probably switch to a CMS driven site anyway.
I haven't built a site that's just HTML for a long time, so I have no strong feelings on the matter. It's really nothing more than personal preference at the end of the day.
I agree with Harry that if you're doing a site that has repeated elements on every page, then it makes sense to break...
Are you asking what extension to give your filenames, or whether to use HTML instead of XHTML?
Extensions don't matter really. Assuming your server is configured for it, you could put "Filename.wibble" if you like :-)
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