I don't have a good answer to the big-picture question, but one trick I've had a lot of success with over the years is building my own suite of life-logging too

I don't have a good answer to the big-picture question, but one trick I've had a lot of success with over the years is building my own suite of life-logging tools. I have my own system for food tracking, TODO list management, pomodoros, chore reminders, clothing and stuff management, contact tracking, a mini-Wiki, link management, and many others. They all connect to and cross-reference each other in helpful ways. If you are a good coder and have a simple web framework, it shouldn't take more than a couple of hours to build a new widget, and in principle the benefit will accrue for years. My theory is that off-the-shelf life-logging and productivity tools don't work very well because people actually have very different lifestyles, work habits, and so on. So to actually boost productivity you need something very closely tailored to your own life.