I've never had a gate agent question me about the WF or even the TS. In my experience, anything that looks like a reasonable briefcase is just passed through without a 2nd glance which includes these bags. I could see a discount carrier (spirit, frontier, etc) possibly giving you a hassle but that's it.

If you overpack these bags, the only problem you might have is fitting them under the seat but you should never have a problem carrying them on and placing them in a reasonable overhead. I fly lots of regional jets and have never had a problem barring a bulkhead seat. As for your list, you should easily be able to fit everything you described in the WF without an issue. The only questionable item may be shoes depending on type and size. Any athetic shoe should compress fine unless they are like size 13+. I would expect those to fit on the front, right side without any problems. The laptop + sleeve and some folders/papers in the back, gym clothes, chargers, etc in the front left and pens, cards, etc in the front facing zippered areas.

Here are some pics of my WF on a recent trip for 1 or 2 nights travel; this was the only bag I took. Sport coat (WF large packing cube), 1 or 2 nights clothes in EC med folder (pants, shirts, under stuff, etc), lenovo W530, toiletries, chargers/gear/power, etc. One thing to add, I would suggest the cordura vs halcyon one especially if you use it professionally. The cordura looks more professional and holds it shape better than the halcyon one.