If you are going to use use Windows Live Writer and WordPress 2.3 it is suggested you install the wlw manifest helper as found at this blog. You may have to have Windows Live Writer redetect your blog. Once done the keywords field should be activated for you to use as your WordPress Tags.
Update:
WordPress 2.3.1 has this built in now.
I’ve finally found something that I don’t like about the Windows Live Writer. The only maps it supports by default are maps from Microsoft’s website. Birds Eye View on Microsoft’s website is a lot of fun except it doesn’t work on Safari. So what I really don’t like is that the bird’s eye doesn’t work on Safari. I changed all the links on my sites that had linked to Microsoft maps over to Google maps which has better support for more browsers.
I’m testing out Windows Live Writer. I think it is a great tool and here are a few reasons why:
works with WordPress
allows me edit multiple blogs without logging into each blog
allows easy insertion of maps, pictures, and video (drag and drop anybody?)
However, I did not see any tag suggestion tool that works on WordPress 2.3.