You have to remember the standard IE user isn't exactly likely to go and set this up, they will have to go into the system and literally click do not track - and I can assure you there will be plenty of websites that simply block users with the do not track setting, making it harder for those IE users who do decide to go down this route. For now it sounds like a launch gimmick that isn't going to gain much traction. (hopefully?)

I've done a couple over time, and I must say as far as skinning Wordpress goes, it can be a bit time consuming, however if you have a set goal of what features your blog etc is going to have you can cut out some time like that, but honestly it's still likely best to get the theme fully complete. As long as you know some basic php and HTML you won't have an issue on the technical side however, but when it comes to time... well that's something only you know how much you have of!