There are two possible solutions to this problem. One is tedious, the other is automated and a lot less tedious.
WordPress doesn’t appear to be robust enough to handle more than 150 static pages. I’ve tried and it keeps crashing randomly between 90 and 150 pages. When WordPress crashes, I lose everything in the MySQL database.
My second objection to this option is that the only solution listed in the WordPress Codex involves writing your own perl script to strip the HTML tags from your existing pages and reformat the HTML pages as RSS items, all in a single file. Once your script has created the RSS file and the RSS feed items, you must then run the file through the WordPress RSS importer.
While I have the skills to write such a script, I don’t have the time. I tried Googling to see if anyone has written such a script and came up with no relevant hits. I tried CPAN and also came up with nothing useful. It also occurred to me that any automated solution has the potential to damage every file in the site, which I also don’t have time to fix, so any automated solution has to work right the first time. Another complication is that I also don’t have direct shell access to the server, so converting the HTML pages at the server to a local RSS file and then using the importer is not an option.
Fortunately, I have another solution which is lower risk and has a better chance of getting the result I want. I can use some of the automation built into Dreamweaver to convert all the pages en masse to the new theme’s layout and style via the Dreamweaver template system.
Solution #2 is the clear winner for me, but the current theme I was using had a problem. Let’s see what that problem was and how I fixed it.