I was petrified to make the move from Typepad to WordPress. I had over 1,000 blog posts and over 10,000 comments. Not to mention the back links. I couldn't afford for anything to go wrong or get lost.
So I put it off for months. But when I heard about Foliovision and saw the size of some of the blogs they'd already converted, I was ready to take the risk.
It went very well and now, a year later, I am enjoying all of the advantages of WordPress and am so glad I took the leap of faith.