I really like Typepad and though I'm giving up things like custom .htaccess redirects for old posts and my old permalink URLs, I'm gaining things like the easiest to use posting UI available and most importantly, I'll never need to update any software by hand ever again.
It's been a long, frustrating week with several days spent trying to move off Wordpress (I was tired of my weblog app chiding me for upgrades every two weeks) followed by several days trying to get MT to work followed by brief experiments with Textpattern followed by giving up and finishing here.
I made the same journey, installing several weblog publishing programs on my server before throwing in the towel because of frequent security and feature updates. I finally decided last year to buy a $299 yearly subscription to TypePad that gives me unlimited hosted blogs, each of which can be published at its own domain, use guest authors, and employ advanced templates.
I'm still publishing Workbench with software that I wrote, but all new sites that I create begin as TypePad blogs. I love being able to turn an idea into a web site in five minutes, particularly when I'm creating sites with other people. Now, when I pester somebody I know to begin a blog, I fire up TypePad and create one for them to show how easy it is.
So far, I've only run into one area where using TypePad was problematic. The service makes it easy to incorporate content from other sites on a blog using widgets, but I couldn't find a widget for adding Google AdSense or any other ads to a blog. I had to put the ad code in a TypeList and give the list an empty title containing nothing but space characters (" ").
This workaround is awkward, because you end up with a bunch of no-title TypeLists containing ad code for different blogs. Finding the code later, when changes need to be made, will be an enormous pain in the ass.
Six Apart has been extremely responsive to new developments in blogging, adding new features to TypePad as they become popular in other publishing tools. It was one of the first companies to adopt the recommendations of the RSS Profile, such as including an atom:link element to identify a feed's URL.