Thanks for the feedback everyone. To give some more background, I have been packing with one bag for a while, using a small duffel or a roller. The duffel is too small for some trips and the zippers are starting to fail. The roller is a Delsey and the plastic support/handle on the bottom broke. I just had to take the bag 2 miles unexpectedly and it was not fun dragging a roller through a city. So I am definitely looking for durability and shoulder/backpack versatility.

That said, I am concerned the eBags Weekender may not last through many trips. Am I wrong? Is it likely to stand up to dozens of plane, train, city, and car trips without breaking? Has anyone used one for a few years?

I'll try to check out the BR 224. That looks like a good option too (not that I need more options to choose from!).

Still wondering if the Tri-Star holds enough or if the Sky Train is comfortable to carry on the back - I noticed it has no waist strap on the photos on Red Oxx website.

Does anyone have experience with the MEI Executive Overnighter?