Windows Live Writer 14.+ is the latest version; has been for almost 2 years. The new version may be coming out this coming fall- you never know with Microsoft.
Connection issues
The issue could be with Wordpress server, or a plug-in. Plug-ins can cause Wordpress to act weird, or malfunction. Try disabling all your Wordpress plug-ins, try your issue again, and see if the problem goes away. If it does, your plug-in problem is confirmed;
then you just need to find the plug-in that's causing the problem and disable [or update] it.
Cross posting
While I haven't tried it personally.I know what your discussing.
http://gallery.live.com/search.aspx?q=cross%20post
I hope this helps...
Until next time,
LEHenryJr
LEHSYS.com
If you this answers your question, please 'propose as answer' for other users.