I've used both Roxio and WMM so I feel your pain. I use Ulead now, which is much more user friendly than Roxio, has more features than WMM, and is much less expensive than Premiere. I think it's around $80.
The only way I've figured out how to sort of do this effect in WMM is to make one clip fade into another for a very very long time. During most of the clips they will appear to blend together. It's not perfect, but it's the best thing I've come up with.
I hope that helped.
~Anna
