I have the luggageworks bag and a "flight bag" aka a laptop bag from staples. I'm actively considering getting a cooler as well but only for a good price, $60 for a black cooler seems outrageous.

two is probably the average. Three is acceptable, but approaching too much. More than three? Son, you ain't a flight attendant.

-One Carry-On (LW Stealth Air 22”, no side pockets/737 style)
-One Flight Bag (LW Tote or Duffle)
-One Personal Item (Cooler).

Plus a coffee in the left hand and breakfast burrito in the right. :D

I carry two. Luggage Works Stealth 22". It's heavy but bullet proof. I also use a MYGOFLIGHT PLC Pro. It's kinda pricey at 200 bucks but has pockets for EVERYTHING including padded compartments for your iPad and a 13" laptop. They also have great customer service as I had the zipper fail on one of the main compartments. All I had to do is snap a couple pics to send them and two days later I had a brand new, updated bag with no questions asked.