Re: What problems could I encounter using 301 mod_rewrite?
Drupal is an acquired taste, and is not for everyone. It takes a bit to get going with it, though once you get rolling with it, it's very flexible. It will allow you to completely follow the structure of the old site.
Depending on your site's structure, it IS possible that Wordpress can be made to work. Maybe.
Joomla has never been very friendly or easy to deal with when trying to import an old site into it, and the urls have never been SEFU, even though they pay lip service to that. Joomla's okay for new sites, though I think there are much better CMS out there than Joomla.
Another option for you would be ModX. The aliasing in ModX will allow you to duplicate site structure.
Or you can simply facelift the static site. But the future really is with dynamic sites. They're just so much easier to deal with on the longterm, and give so much more ability to keep a site fresh and content rich, which gets you up there in the SERPs much quicker. And with future redesigns, if you want a facelift you simply drop in a new skin, and the whole site is DONE. None of these site structure worries like you're having now.
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