However the techie in me had to dive deeper. Why weren't my posts with pictures succesful? I found the answer on the Live Writer MSN group. It was a bug to be fixed in the next release.
Guess what happened today. Live Writer 1.0 Beta was released. I LOVE short release cycles. And yes my posts with pictures now pass through to my Live Space.
Cool to check out is also the plugin gallery. I have an idea myself but won't tell untill I'm ready. It's a real goldmine 😉
Now I configured my MSDN blog account too, I hope to be blogging more frequently again.