and if yes, to then invest my time into trying to create a solution.
Hmmm... I think "investing time to look for a solution, which will then look for a problem". I think back to the time in my life when I was a student, and I rented. This was a time when every telephone was connected to the wall by a wire, and a VOR was a modern navaid. I had no problem writing my bookings and lessons on my calendar. I kept a paper pilot log, and training record. My flight planning was done, as needed, on a paper form, which I took with me in the airplane for the flight.
I admit, I use Excel now to maintain my pilot log (it does all the sums nicely!). I use Foreflight if I need to flight plan ('cause paper charts seem hard to get these days), and I use GPS as a reference to flights I have planned ('cause I'm lazy about ETA calculations). Over the decades of flying, and providing a lot of advanced GA training, I have learned to be wary of trainees who come out to the airplane tech'd out to the max, and seemingly dependent upon "solutions" to aide their flying. I observed that in some cases these were a distraction from the task of managing a flight in one's mind, being mentally prepared, and the executing the flight from skill and experience rather than aids. My worst example of "please put that tech away" was when I told my candidate that we would not need his Ipad for circuits that day (as it blocked my use of dual controls. I put it in the seat back pocket for the flying, to find that my leaning back in the seat had broken it - Oh well, we hadn't needed it anyway, and I paid for the Ipad. Sure, if you're planning a Transatlantic ferry flight, there's going to be a lot of planning, and a bunch of tech. If you're flying to a new place for the $100 hamburger, a review of the chart, W&B, and flight plan, along with notes about the airports. If you're flying circuits, W&B, and the frequency, then focus on your piloting skills - don't distract yourself with needless tech.
If you are an active, aspiring pilot, there is so much you can learn to maintain and advance your skills in aviation, my advice is to devote your time to those aviation disciplines, rather than trying to devise a tech'y solution to something that generations of pilots have managed in mind, or on a straight forward personal calendar.
1) How do you manage all the admin and planning in your flying life today?
2) What are the biggest friction points or inefficiencies you notice?
3) If you could design the “perfect world” setup, what would it look like?
I write any necessary flying responsibilities on my calendar, and review tasks and expiry dates every month or so, to assure I keep everything current (including owning the plane)
I happily have no friction points in flying at all. If anything, I find myself thinking (as yesterday) it's been a week or two since I flew the plane, so I should take it up for half an hour - no friction going flying.
My perfect setup (for GA VFR) is Foreflight if I need to flightplan, review paper documents for validity and correctness, check weather in the Environment Canada/NAV Canada websites, maybe use a handheld GPS in flight, and record my flying in Excel, and the airplane logbook (paper) after I fly. If I plan a big trip, I check everything before that flight/trip. If needed, I document a plan for the flight on paper (perhaps printed from MS Word, if I typed it out). So, for me, I have found the perfect setup - simple.