Yeah, I came to the same conclusion as far as optimizing for two carry on bags.
My setup is really simple but works for me for months at a time. I have a tri fold clothing bag (an old Patagonia burrito, which they sadly don't make anymore) that's for clothes, grooming/hygine, etc, and then a messenger bag that's for laptop, kindle, headphones, emergency rain gear, medications, other similar things.
It may not work for everyone, but I found paring down to essentials was very worth it. I never have to worry about checked bags going wrong. I can wear both bags comfortably while walking for a couple hours, so if I'm moving locations or can't check into my accommodations yet it's no big deal.
One thing I like about this setup is I don't look like I'm hostel hiking. I just look like someone in business casual with an extra overnight bag. It's not fair or just, but sometimes this makes the difference about getting hassled hanging out somewhere with wifi for a couple hours.
The tri fold is roomy enough to pack a suit and plenty of casual clothing. I just hang it up when I get to my room. Unless I'm wearing or using it, items go back to their place in the bag. I never have to unpack, pack, or worry about leaving something behind.
A few simple tricks can make a big difference, but they're probably pretty personal. I pack a lot of extra socks, undershirts, and underwear, all made of thin wool. This helps me stay fresh if I'm a bit long between laundry services. In my electronics bag I carry a short extension cord, some USB plugs and charging cables, etc. That'll make you the hero in every cafe you go to.
In any case, my big takeaway was that I just don't actually need much stuff to be content for months at a time.