I just received this set to use on a four-day trip to Puerto Rico in February. I need it to fit clothes for a wedding, as well as hiking clothes for a little sightseeing. This suitcase looks like it will do the job...
The roller *should* fit as a carry-on bag, plus it is hard on the backside but soft and expandable on the front, which I really like. The pop-up handle is light and easy to push up and down, while my old roller was a lot clunkier. The inside is lined with a really dark pink fabric.
The duffle bag / large purse is also really nice. I should be able to fit my regular purse, plus more clothes and even the toiletry bag inside, and still fit it under the airplane seat. The toiletry bag itself is awesome, very similar to the kind of organizers that LL Bean makes. It can't fit full size bottles, just trial size liquids, and it even provides you a clear quart-sized zipped bag for airport security.
I will say that the picture on Backcountry and on the Dakine website is a little misleading in terms of color. It is a dark navy, with really dark pink (almost a cranberry or mauve color.) I actually like it a lot better than the picture, which makes it look like a bright pink.