Ended up pulling the trigger or the Teranishi Venture LT. I will be sure to follow up with some use pictures and feedback once I get it on hand. Thanks again for all the help!
https://www.teranishistudio.com/collections/stocked/products/venture-lt-tobacco

Anesthetist, can you comment to the comfort of the leather straps on Teranishi when loaded up/heavy? The more I look at the Venture the more I like it, but it's a lot of money to drop if it won't be comfortable when loaded and I'm trying to walk a distance. If the lack of padding has never been an issue, that will help make my decision a bit easier.

Thank you for the ideas, these are all very helpful.

I had considered the Teranishi Venture, it does look gorgeous and has some nice organization options, especially for a ruck. I am concerned about the comfort of leather straps vs. padded, especially with heavier loads. Is this a justifiable concern? Same goes for the Tanner Goods Voyager, looks really nice but I have concerns about the strap comfort.

The Trakke looks really nice too, I wonder if the buckles end up being annoying to use over time. They look simple enough, but it's hard to tell in an actual use case.

The Millican Wainwright is intriguing, and I had also been considering the Topo Klettersack, but the style may be a bit too outdoorsy for the workplace.

Hey, I am currently looking for a bag myself and this thread has been extremely helpful in generating ideas. Primary use would be to go to work (I am an engineer) and classes (I do my MBA in the eveninging), but hopefully the bag could double as a smaller carry on if needed (doesn't need to be a weekender bag but that would be a nice bonus). I primarily drive places due to where I live, biking to get around isn't the best option. I'm not super tall (5'7"), so if the bag looks small, that may be okay. I originally got a Waterfield Staad backpack, but found it to be too wide for my frame and too slim to hold much of use.

• I really like the waxed canvas look.

• I would like to avoid traditional buckles; I have a leather messenger bag but do not tend to use it because the buckles make it take too long to get stuff in and out.

• It needs comfortable straps, sometimes I lug two laptops around and the bag can be heavy, so no all leather straps ideally.

The items I am currently interested in are the Bedouin Delireis, Azo Equipment Amhara, and the Kletterwerks Flip. If anyone has input on those bags or ideas for others, please let me know. I considered the Goruck but decided the more technical look was not what I wanted for the workplace/class.