Sounds like a no brainer with the after sales service at the 2 local Trek stores.

I don't know how "safe" Madison is for locking a fairly expensive bike up but I'm no fan of expensive bikes for commuting for that reason. If I were in your shoes, I'd get 2 bikes.

(1) I'd buy a used bike (probably a rigid mtb) for commuting and esp. for lock up duty. Those tend to be readily available and inexpensive (less than $200). Don't forget you need more than just a bike for a commuter. You will need lights, a lock, fenders, bags, etc. That can drive up the costs pretty fast.

(2) Then I'd buy a bike for riding and buy it 2d hand to keep the total budget at around $1300.

Failing that, the Trek seems like a no brainer choice given the before and after sales service in Madison you described.