David, it's a good list! 8 pounds is nice. I'm not very familiar with Wisconsin weather, but here's my two cents...
I don't know how much of an issue your budget it, but you could save some money with water purification by getting some aqua mira instead of a steripen. Steripens are nice though, but I would make sure to carry something for backup too (AM tabs would be good).
It looks like this list is good down to low temps in the 30's. With a quilt you'll want a balaclava or beanie. IMO, the Patagonia Houdini is a little unnecessary. I'd swap that for a long sleeve merino top, something around a 200 weight. I know its a totally different piece, but I think you'd use it more.
A not too expensive upgrade from a blue ccf pad would be to pick up a thermarest prolite short or a BMW torsolite on gear swap, you can usually find them for around $35-40.
A pack that is similar to the SMD Swift is the new Osprey Hornet, and you can probably find one in a local gear shop to try out if you wanted before you bought it.
If you haven't tried on the inov8s yet, I'd try to find them in a shop to try on before I bought them on amazon. I know a lot of people love them, but every shoe fits every person different.
You'll add in a few essentials too before you hit the trail that will inch your weight up. First aid/emergency kit, map, phone, camera, keys, toiletries, etc.
Good luck with buying that new gear too! Buying new gear is the funnest thing ever!
EDIT: after thinking about it, if you'll be biking with this list, the Houdini will be a great piece actually. I'd still add a long sleeve baselayer though.