Scouterman,
Merry Christmas to you. I am a fuller-fuller figured man so I understand your challenges with finding a backpack. And I also commute to Philly each day and have to carry both EDC supplies and work gear (laptop, files, etc). My strategy is to carry a smallish kit of essentials with me and a full BOB kit in my car.
After many backpacks and messenger bags over the years I have settled on a backpack by Tom Bihn. Messenger bags don't work for me because, frankly, I carry to much stuff

So after research I purchased the Brain Bag (
Tom Bihn bags ) along with their laptop sleeve and snakecharmer. It's a great pack, well made and sized for people like us. I don't know about the size of the waist strap (I know it doesn't fit me, but I am larger than you) but I they have excellent customer service. The build quality of the bag is first rate. This backpack survived 1 1/2 years commuting in and out of NYC and is still going strong 6 months into my new commute. I expect I will fail before this bag ever does.
As a pack it is relatively simple, three outside pockets, two main interior divisions. The larger outside pockets have pen holders and such in them, but otherwise the bag "an empty canvas". The main compartments each have two strips of webbing sown into them (about 1/2 inch wide). They are designed for the clips for their laptop sleeves but I have used them to clip lots of things. And TomBihn will send you extra clips if you need them. The back is padded and ventilated and very comfortable. Loaded my pack is about 18 - 22 pounds and I have carried it for two hours or more commuting without a problem. It's also gone through some thunderstorms waiting for the train without getting the interior contents wet.
I keep my EDC supplies in a pouch that my daughter made, tucked below my laptop sleeve.
If you are looking for other ideas back on Dec. 1 I posted a question to the forum on what else I should include (
Commuter EDC kit http://forums.equipped.org/ubbthreads.php?ubb=showflat&Main=10094&Number=114448#Post114448)
and got a lot of great responses.
Best of luck in the new year,
Kurt