I've had my black / iberean nylon Pilot for about 2 or 3 weeks now and mainly using it as my work bag.
I work in an environment where button up shirts and ties are the norm, with suits every now and then. I also sometimes have to travel via plane for work, and have used the Aeronaut and the Pilot together for those short trips.
So far so awesome.
Black doesn't draw attention and looks professional enough for my purposes now. The bag also maintains it's shape well, which adds to the "professional" look. I don't think a dymeena would be suitable in terms of look and style in the environment that I work in. I'm working in a 2nd tier city in the developing world, and when I travel I usually go to other 2nd tier or even 3rd tier cities, so it's not like everyone around me is wearing armani suits and carrying fancy leather briefcases. In these environments, the pilot looks plenty nice as a work bag. If I were to move to say, a Tokyo or London or Singapore I might consider a more traditional slick looking leather briefcase to go with a suit. I would do it grudgingly though... The pilot helps me stay so organized!
I have the standard strap. I also own the Absolute strap for my Aeronaut, but that would surely be overkill for the Pilot. For one, the strap wouldn't look good because it's so large. Also, if you're packing the pilot so heavy that you need the extra support and comfort of the Absolute strap you're probably doing it wrong. The standard strap is fine.
I have the tiny parapack pouch that I use in the back portion of the Pilot on the O ring to hold my keys.
I have a small padded pouch (that was actually way larger than I expected) also in the back portion on the other O ring to hold my watch after work or when I pack it up to go through airport security.
The back portion also easily fits folders and regular A4 sized papers and whatnot.
The front side pockets fit my Kindle paperwhite which is inside of a thick Oberon Design case easily. The same pocket also fits my work phone in that padded area. In the other side pocket I have a small dymeena pouch that holds some essentials like my earbud headphones and... stuff. I always keep a Tide stick in one of the pen holder areas, and some hand sanitizer in the pocket next to that.
I regularly keep a water bottle in the center pouch.
I don't use any packing cubes with the Pilot and can't imagine that I will ever need to.
That's pretty much how I roll.