As far as the flight bag, you're not going to need wheels on it if the bag you have has a hook. That's just weight that's going to waste.

As far as the bag, why do you need a garment section? That's what the coat closet/hooks up front are for.

I'm pretty minimalist when I pack. I have a 22" strongbags roller. It's a little more pricey than the Travelpro, but much better built and much less than luggage works. So far it's held up well to commuting.

In both cases, you get what you pay for. If you spring for a coyote works kit and luggage works bag you're going to be out $800. Spend $200-300 and you might have to replace stuff every couple years. You see plenty of people using cheapy stuff and getting years of use out of it. I decided to try and go for the middle of the road versus all out because I had a cheap bag break on me while on day two of a four day and wanted better than cheap without breaking the bank.