Hi MM, some great tips for sure.
Hang your neck pillow from your luggage - decreases space in your carry on. Some come with snaps already for that purpose.
I've got a fantastic neck pillow by Caveau, made from memory foam that rolls up into about a third of its size, and fits inside my personal item. It gets really warm, which is its downside (they've subsequently made a "cooler" version). I've seen many folks with their pillows tied as you suggest, and if I wasn't going with a personal item that's what I'd do for sure.
Try a couple of different ways to fold your clothes. I'm not sure if you tried packing cubes.
Yup. I'm an Eagle Creek fan and I have about a half dozen that I've used in the past, but they've sat unused for many years now since I learned bundle packing. Now that I'm learning to pack really light, I think it's time to take them out of storage and do a serious test-pack with them and see if they help.
If you have a windbreaker for rain or for days you tour a city but a sport coat is too much to wear out and about, take that too. Of course, that would pack thin, and your sweater or a sweater vest can layer underneath.
I'm going to look for a nice, stylish windbreaker that can add warmth this week and consider leaving the sport coat at home as many here have suggested.
If you still plan on the 22" as your carry on, AA allows a personal item of 18 x 14 x 8 inches (45 x 35 x 20 cm). Some soft-sided laptop bags with the above dimensions can fit not only the laptop, chargers and other accessories, but maybe a polo, a day's undergarments and your 3-1-1.
Normally that's what I bring on airplanes. My 22" (usually in the hold or gate-checked) and a leather briefcase/messenger bag. It fits the personal item rack at the gate, expands nicely and I can stuff everything into it. I just find it's a bit heavy, and it doesn't fit my new, smaller/lighter laptop as well as it did my old 15". Plus it hurts my shoulders after a while when I have to drag it around airports and trains. The ideal bag will slide over the telescoping main bag handle. The tote I have does this and I love it (plus it makes a usable day bag in a pinch), but it doesn't fit the laptop, so I'm still searching for the perfect bag. I might just throw the laptop into the 22" (it has a compartment for that) and use the tote. That's "Plan A."
United Airlines has smaller measurements for a personal item. So since you are flying both, I guess the larger personal item is not an option. UA personal item dimensions are 9 inches x 10 inches x 17 inches (22 cm x 25 cm x 43 cm).
Mine is 15 x 9 x 9 if fully stuffed, which it probably won't be. Its main use will be for the pillow, my folding cane, Bose QC-15 noise cancelling headset, sunglasses and spare eyeglasses, 3-1-1 bag, medications, maybe a few snacks, an umbrella, USB charging cable and post-security water bottle. I also use it to throw my pocket contents into before TSA screening (phone, wallet, keys, etc). Its main use will be for everything I need from the moment my wife drops me off at EWR until the door closes behind me at my hotel in Munich, and the reverse trip, from my Prague AirBnB to getting picked up in NJ (including a 6-hour layover at Heathrow). I'm used to doing it this way since the 22 is usually in the hold, and this method has worked very well in the past, albeit using my leather briefcase instead of the tote.
Packing is a lot of trial and error. Do some mock packing and dressing.
That's the plan, for sure. I'm comfortable living out of a suitcase, only it's usually a much bigger and more heavily-stuffed suitcase.