I have and love the Timbuk2 Wingman.. some points to consider:

As a duffel, it doesn't work well. If it is packed and you hold it by the side handle, it will not stay straight. The bottom will kind of come in, towards your knee, and just under the handle it goes out a bit... kind of hard to explain. Holding it vertically solves the problem but the bottom might rub the ground if you are shorter than 6' or don't hold it higher. Wearing 1 strap on the shoulder doesn't work due to its size/shape.

As a backpack, it's great. It can definitely pack a lot... more than what you'd like to carry on your back for sure! I love compartment on the bottom, that I use for a pair of shoes and toiletries, the top compartment serves well for travel documents, a small tablet. Laptop and paperwork goes in the laptop sleeve.

I don't like luggage/bags that don't have shape. I cut some cardboard and lined the inside, both sides and the top (standing vertically), making kind of a hard shell around it. I wish this came built in, but it works.

Pros: holds a lot, love the compartment setup, hard bottom (suit-case like)
Cons: doesn't carry well as a duffel, personally would prefer if it held shape better on it's own


the tri-star looks nice and i love the compartment setup