This have been my daily carry for a while now. How much of it I bring depends on the situation. I usually bring either one or two pen cases. Usually the senseBag case and the Nock.co Sinclair.
In either case I usually have a gel pen, currently 0.4 mm Zebra Sarasha Clip, one wider nib and a finer nib. The finer nib is for general writing and the wider one is for underlining and drawing boxes around things.
I also always have a pen stuck in the loop of my Hobonichi cover to keep it shut, this is often my Pilot Custom 823. And I always have my Vanishing Point with an EF nib unit in my Nock Co Seed A5 notebook cover.
The most used pens in addition to those two is my Sailor Pro Gear F and my TWSBI VAC700R EF for general writing, plus my FC Pocket 66 with a music nib and my Lamy 2000 M as the underlining and drawing pens.
I usually go with them because they just work and have plenty of ink. When I’m at home I often do more of a whatever I feel like using from my pile of inked up pens.
The Lamy Safari found itself in the Hobonichi loop a lot when I was testing out that, and I suspect it will become a part of my regular carry very soon.