Just got back from Chicago - I checked a 22" roller and used my OMG for carry-on, with a purse (typical LeSportsac hobo - I love the light weight for travel) as my personal item. I like the OMG - I really love how it fits on the roller so nicely through the airport! But I'm used to a much larger nylon tote as a personal item (with a 20 or 22" roller combo) so it did feel small. I was only gone 4 nights so I didn't need a ton, but I felt a little crunched anyway. I didn't see a way I could have used the interior "shoe" bag either - would have taken up SO much space. And I decided not to take my laptop on the trip, thank goodness, because I don't think I could have made that work.....
I was doing really well at traveling light for a few years and have "crept" back up lately. Need to work on that!!!
The bag itself is still gorgeous and I adore it ;-)