I used this system for the recent Sonoma Coast workshop, and it worked well.
I treated myself to a Peak Design Everyday Carry 30L before the trip, as I wanted something large enough to accommodate two bodies with lenses attached, my MacBook Pro 14" and an iPad, with a little space left over for a jacket and a water bottle. This served as both my carry-on and my personal item for the flight and slid underneath the seat in front of me; no need to jockey for overhead bin space. Outside of Safari West, where I brought the backpack with me, I used my beloved Think Tank Story Teller 8 as my walkaround bag. I packed it in my big checked bag, where it held some books and snacks.
There was one flaw in my system: weight. I'm typically not an over-packer when it comes to local photo shoots or even vacations. I'm good with one body, an all-in-one zoom plus a fast prime or a compact camera for a more compact low-light solution, and often just edit on the iPad.
But since this was a photo workshop with a safari experience, I brought my Nikon Z 100-400 on my Z7II as I didn't want to constantly switch lenses. That combo delivered in terms of image quality, but full-frame was not my friend when it came to weight. I also didn't want to rely on my aging iPad as my editing machine, and while my MacBook worked flawlessly, it wasn't exactly light. Add a bundle of charging bricks and cables, spare batteries, a water bottle, and a fleece jacket, and let me tell you, I struggled to lift that backpack - never mind wearing it - and literally had to put my arm through the second strap and hop up in the air to launch it onto my shoulder.
In retrospect, I would have been better off with something like the Nikon Z 28-400 (which I don't own but could have rented or borrowed) or my OM-1 with the 40-150 and the 1.4x teleconverter. It would have been a good excuse to buy the new iPad Mini I've been wanting, too, which would have allowed me to leave the MacBook at home.
My two big takeaways were that there is no perfect solution—everything is a compromise—and weight adds up quickly, which isn't news to seasoned travelers or hikers. Regardless, the two-bag system is definitely the way to go for photo-focused travel.