Windows Live Writer inconsistent with Media Library

You can make WLW upload images directly via FTP, you can set this up in settings of connection to your blog.

However as long time WLW user myself I would strongly suggest you to try and make sense of media management in WP, even if it seems excessive at moment (it did to me for a long time). Down the road you will very likely come to some things that are much easier done with media library, rather than organized bunch of directly uploaded files.

I know this very well myself, because I am facing need to re-organize and import three years worth of media at my blog. 🙂

PS WLW is fine, but do try writing posts in WP itself. A lot of work went into that part of experience and it is very impressive by now.