I have a friend, who started his website on TypePad. *GASP* I know, but he's not overly technical and TypePad allowed enough control over the site, while allowing him to run ads. It's not a huge site, but it's gained some popularity. You can see it here. http://www.wooohah.com/
He is now realizing he needs to get some more control over the features of the site, but he would still need to manage it himself as he is not large enough to just pay someone to do it. There are a couple of issues that I don't know how to answer for him, and I was hoping someone can help me address them.
1. What imports over to WordPress? Posts? Pages? Comments? Categories? Tags? I believe the standard importer takes care of this, but I wanted some confirmation.
2. Permalinks are going to be an issue. If you look at his site, his permalinks are set up a certain way, and unless he copies that, all links that people have to his site when he transfers won't work. Any ideas? He'd prefer to not have to rebuild his ranking from scratch.
To sum it all up, he doesn't want to lose traffic, or as little as possible. So if you have any suggestions, I'm all ears.