score:3
As a road warrior myself, I try to carry as little as possible.
For shorter trips ~5 Days, I now prefer to take just a backpack in the 40L range. Similar to this one: Wander Pack. I really like having the separate shoe/dirties compartment. Backpacks are also much lighter than rollers.
If you do go the backpack route, be sure to have one with stowable straps in case you do want/need to check it. The airlines really, really don't like dangly things.
Paired with a tech vest such as the AyeGear V26 Vest and I'm all good. Even for longer trips if I can do laundry.
For longer, multi-venue, special activity trips, I take a large rolling duffle which must be checked. I did the overhead spinner thing for a long time and now find the backpack is easier to handle.
Upvote:2
If you want easy access to (some of) your stuff while you're in the air, Choice 3 would allow you to store the messenger bag at your feet, under the seat in front of you. I travel this way, with all my can't-lose stuff, like medicines and computer, in the small bag.
If you want to carry all your luggage on board (to avoid the time sink of waiting for the luggage carousel upon arrival), make sure whatever bags you choose fit the airline's carryon size and weight limits. On the other hand, the convenience of checking a larger bag through for a two-segment flight may outweigh the quicker exit if you carry the larger bag with you in the cabin.
Finally, if you're not eager to wear a loaded backpack as you trek through the terminal and onto the street, choose a rollerbag.