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Move a chunk (50?) of the 200+ and don't try to change how WordPress writes the URLs.
I am pretty sure that there is an importer plugin out there that will let you grab all your html from your static site and will convert it into wordpress posts.
I remember using it on a site and it was OKAY but that site had so much BAD html* that it took me a while to get everything cleaned up.
You did put all your content into a single, consistently named div, right?
1. My html pages follow this link structure:
www.mysite.com/home-improvement/study-room.htm and so on
I think the last time I needed to get a sitemap for an html site, I used Xenu link sleuth
You can do the same using cut and paste a few pages at a time, inserting pic links as needed, etc., redirecting, and not going nuts.
How did you do the original html to text transfer stripping out the html tags? What program did you use?