Furrygoat.com is going to turn 3 next week (first post was Dec 1, 2001). Over the course of 3 years, I've run CityDesk, MovableType, dasBlog and now Typepad. Every time that I've switched software, I've encountered the same problems, so here's some observations from the latest move:

• Permalinks: They aren't. This bothers me to no end since I have 1100+ posts. It's just near impossible to migrate them without writing custom tools between the different blog engine's. Typepad also doesn't allow custom 404 pages, so this time I had to basically post a dummy page at http://www.furrygoat.com/PermaLink.aspx to let people know that an old permalink is invalid. Perhaps I'll add in a site search there to make it easier for people to find what they're looking for.
• RSS: I would have loved to have been able to set up a permanent redirect from the old RSS feed to the new one - it just wasn't possible. With this move I went from a self-hosted website to the Typepad servers, so there's no way for me to set this up.
• Import and Export: Fortunately dasBlog has source code available, and I was able to quickly write an application to dump entries and comments out to the Typepad Import format.
• DNS Remapping: This caused most of the outage yesterday. I made a small typo on one of the records pointing it over to Typepad, which caused a DNS failure for anyone accessing the site yesterday.

Bottom Line: It's not easy to switch blog engines and seamlessly maintain the user experience.

At one point yesterday, I almost abandoned the whole migration just due to my frustration. While more and more are beginning to recognize the power of the weblog (Scoble has a great example of a recent visit to a winery and the possibilities), I can't imagine what the 'average' user could/would do to get their data from one place to the other (I somehow don't think my dad is going to write a custom export engine).