J.F.
We travel a lot, both across country and internationally.
One wheeled carry on and one backpack should handle all your needs for the trips you describe. That's your one carry on and one personal item (the backpack that can fit under the seat). We just got back from a week in Oregon, and each of us just had a small carry-on and a backpack (husband had briefcase). I was able to fit all of my clothes and five pairs of shoes!
Get TSA pre-check, if you have the time. It's cheap, good for several years, and allows you to leave your shoes on and go directly through screening. Otherwise, you'll have to take your laptop out to go through security.
Use TSA-approved sizes for your hygiene and toiletry items. Put all of the liquids in one quart-sized zip-lock bag so you can easily pull out for security. I usually don't even take mine out of my backpack, but that may be because of the pre-check. But just in case, you want to be ready and not hold up the line. Plus, it's good to keep the liquids (shampoo, etc.) in a zip-lock, just in case something leaks.
Some of the newer plans have the capacity to charge, but you'll have to know what plane you'll be traveling on. When you book your flight, you can check with the airline. You could always get a second battery or carry a portable charger, or you could work until your battery runs low and then read, work on puzzles.
I have a family member who travels with a medical device. In the past that has never counted as any of her luggage, but again, check with your specific airline as things change quickly in the industry.
Check out Allbirds shoes online. My husband brings his on all of our trips. They are super light and comfortable. Great for packing because they don't add much weight to your bag.
Have to go make dinner. If I think of anything else, I'll add later. Hope you have great trips!