You're not alone -- there are a lot of people who dislike change (hell, I'm still using a multichat client that was EOL'd in like 2005 or so, because I hate the user interface of every alternate client I've tried with the burning passion of a thousand suns), but I do honestly think there are ways to improve and modernize things without a) pissing your userbase off, b) screwing things up ten ways to sunday, or c) making it worse than it was when you started. It all revolves around making sure that the changes are done in an organic way, that they add value rather than making things new for the sake of making things new, and carefully observing the actual behavior of your users instead of what you would like that behavior to be in an ideal world.

I mean, there are tons of things about DW (and about LJ, since we inherited a lot of them) that are a usability nightmare. We don't notice them, for the most part, because we've been using them for ages, so we've trained ourselves how to make them work -- but someone new looks at it all and runs screaming! Our overall goal is to improve those usability disasters, while at the same time not losing what makes things so special, you know?