I've got six years of DasBlog entries in my /content directory. I don't have time to maintain my blogging infrastructure (it's hard enough to justify the time I spend just writing the darn thing). For whatever reason, DasBlog and my hosting company just don't seem to get along ... problems with the comments, problems with memory consumption, I dunno...
My only caveats are: I want it to be locally hosted, I want to customize the templates, and I don't want any limitations against uploading other types of pages via FTP (i.e., static HTML pages or ASP.NET programs or whatever).
If you have an opinion on the pain or ease of switching from DasBlog to WordPress, please leave a comment or send email.