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The above design would be better than a slightly bigger rando bag, for balance and weight distribution purposes.
Oh yeah I went with the Surly Nice Rack in the end! Expensive but worth it. Both yourself and Tim had recommended it so thats another gold star from me in your book along with the Makita.
dubkev
How much stuff you do need to carry? I've got a bigxtop front rack bag (like the rando bag but a little larger). It's got d rings either side so I use a padded camera bag strap with it when off the bike.
It's not as comfortable as a messenger when wearing it on the shoulder but it's not bad.