I'm sure you look much nicer while traveling than I do...

I don't check a bag anymore, just have a tiny spinner carry-on and well-organized backpack. This for 3 weeks in places like South Africa and Madagascar, or Borneo and Singapore. So, clearly I am not packing a business suit and dress shoes; it's all lightweight layers of clothing that are quick-dry. Laundry service is cheap in such places. Still, I did a week in Toronto and Montreal the same way, but more urban type of clothing. My co-travelers joked that I was like one of those clowns who can pull endless numbers of items out of a tiny suitcase. I don't use packing cubes as they just take up space.
1 - I roll dresses and shirts to maximize use of interior space, flat-fold undies into the exterior flat zipper pocket, stuff bras, socks, and hairbrush to fill the odd corners.
2 - I am very strict about the wardrobe -- all things must mix and match, allowing the pieces to seem like a lot when I simply mix tops and bottoms for different looks. Use local laundry on long trips. Start with a list, then delete, delete, delete until I have the bare essentials. THEN pack - takes about 20 minutes.
3 - Camera, medications, passport, sunglasses and other essentials go into the backpack. I also pack a small flat zip purse to use while at my destination so I don't haul the backpack into nice restaurants, for example.
4 - Wear the heaviest shoes and jacket (if I have to have them) on the flight. I rarely travel with more than 2 pair of shoes, never more than 3.
5 - Many hotels provide adequate toiletries. Depending on the destination, I may not need to pack shampoo, conditioner, lotion. I pack travel-size products and leave them behind at the end of the trip.
5 - Gifts are usually textiles -- easy to pack. Sometimes I have to carry a shopping bag on the flight home, but that's not a big deal. Many stores will ship items for you. I confess I have hand-carried large "finds" home a time or two, but it should be avoided.

A recent flight had very severe weight restriction for carry-on bags. In that instance I had to remove my laptop and check my bag.

I doubt my methods will work for you, but it's good that you are facing the need to simplify. Good luck and happy travels!