A while back, I started a new job requiring regular travel. Most of my trips are pretty short. Two nights is typical, and three on occasion.
After much perusal, I had decided on a Western Flyer and a Cadet. However, with all of the "stuff" I end up carrying for my job, the Cadet was just way too small to carry when I travel.
Because a big part of my job involves one-to-many presentations and hands-on events where I have to be ready to present in any room with any equipment, I travel with an Apple TV, an Airport Express, and a variety of cables and dongles to be ready to rock and roll. I've got my presentation kit pared down to the basics since I've been into the job for nine months and that all fits into a Snake Charmer with room to spare.
When the Synapse 25 came out, I was intrigued. I hadn't carried a backpack in a long time because I didn't think it was "grown up" enough for a professional to carry. But after ordering one and test-packing my daily carry, I was sold. Mine is black and wasabi so it looks very professional, and I have since gotten over any concerns about what I carry into meetings. So since the summer, I've carried a Synapse 25 as my daily work bag whether I'm on the road or just attending meetings locally. I find that the combination of the S25 and the Western Flyer works for my needs about 97% of the time.
I should probably do a "what's in my bag" video to show how and where I've packed everything, but I have a couple stuff sacks in the side compartments, the aforementioned Snake Charmer in the bottom compartment (Perfect fit, btw. Well played.), my business card holder and Bose in-ear headphones in the small front pocket, two iPad minis in the water bottle pocket, and a Grid-It in the elastic pocket in the main compartment. I'm not thrilled with the Grid-It because it tends to be too "flexy" if it's not held flat.
A couple times a year, I go to a week of training and when it's four nights, I just can't squeeze everything I need into the Western Flyer. I'm sure that a Tri-Star will be coming down the road, but for now I just go to my rolling carryon for those rare trips.