I am going to manually convert my old MT blog into WP.
What I really like about MT was that YOU got to determine just where the images went upon upload and on the fly:
With WP all I see as options are:
with the month / year option
So I wonder if uploads could be renamed to 'photos'
and if I can add folders to that at the time of uploading..
And if down the road I want to use something like Next-gen would having renamed the uploads folder be a real problem.