I was wondering if someone could offer some insight as to whether or not the alteration of the HTML file names in my site would cause a negative SE effect. My site has pages indexed and crawled regularly by the SEs, but I'm afraid that if I change my filenames that the missing pages will be grounds for penalization. I don't think too many users have established bookmarks to my pages. How much impact could missing files produce? Would a custom "File Not Found" page help in this case?
If you change the filenames, you will lose whatever PageRank has accrued to those pages. If you do a 301 redirect for each changed filename, human visitors andf spiders alike will be automatically taken to the new pages and in due course the PR previously earned by the old pages will be "reassigned" to the new ones (but it will take a while for that to occur).
Yes agree'd with Web Gazelle. if you must though, 301 re-direct is the way. This way you are guarantee'd not to get any missing pages and also not to get any duplicate content.