Jean, thank you for that writeup And enjoy your family this weekend!
You make some really good points about the value of TripIt. The flight details that you receive from it sound like the pro version?
I also don't use TripIt very often during my trips. I use the resulting synch with Google Calendar quite often, to answer questions like "which day is my food tour?" or "what time is my dinner reservation?"
My best use case of TripIt was when I (earlier this year) rescheduled a trip from spring to fall. I booked the wrong return flight date and realized it when I saw in my revised Google Calendar feed (from TripIt) that my new flight home was before my 2 extra nights after the end of a tour. Thankfully, I figured that out in time to change the flight, and even saved a (tiny) bit of money with the reschedule.
I use OneNote for the details of my daily itinerary, such as "what time is the hotel breakfast." There can be a lot of that with my typical weeklong city stays.
I also like to use Wanderlog for my spatial planning for a big city visit - figuring out which sights are near each other. While I use it for that early trip planning, I haven't incorporated it well into my trip execution. But that's a discussion for the August 22 Wanderlog session!
https://community.ricksteves.com/travel-forum/travel-meetings/tech-for-travel-talk-sat-aug-22-getting-started-with-wanderlog-for-travels-online