Any recommendations for a rolling bag that will fit under seats, $300 would be max budget? This is a strong requirement as I try to avoid checking bags as much as possible and traveling with a rolling bag for clothes as well.

Primarily fly AA and most of the times is 737 or A321.

I typically travel with 2 laptops, sometimes 3, extra monitor, battery bank, steam deck, and then all the wires to go with it.

As I am getting older it is just too much to carry all the time in a regular backpack and back always so sore on travel days as well as taking it in and out of office while traveling.

I already have a roller bag so ideally something with the elastic strap so I can place it on top of roller bag when traveling with both at the same time.