Pennsyltucky? Isn't that WV?
In answer to your question, mod_rewrite is VERY powerful because it uses a regex engine to capture information and use it to redirect. However, nowhere in your post did I see that you were retaining the same data in your links in your new structure to allow capturing variables and using them to redirect.
You might benefit from reading the mod_rewrite tutorial linked in my signature as it contains explanations and sample code. It's helped may members and should help you, too.
That said, you have two options: Redesign your new site's links to retain some/all of the link information from the old website OR use a RewriteMap (probably use a "handler file" for the redirect) to redirect EACH of the old pages to their corresponding pages in the new website (with permanent redirections so you don't have to go through this painful experience again).
"Speficity!" There, I said it again. More information about your links (that they can be used in redirections) or not; how many redirections (pages) are being moved; etc., the better the answer you'll get.