IMHO you are making the same mistakes that I did when I was younger and even more OCD.
Don’t try to plan your Adventures like a Google Map trip to Grandmas.
Pass by a Dirt Road, turn down it and see where it goes. Hit the Record button on your GAIA App, run it out, make notes and save it to do again, finish or drop a pin at it indicating NO GO.
All sorts of sayings etc. It’s about the Journey, Not the Destination.
I use to drive my wife crazy with having everything planned to the last step on a Hike or turn on a Trail.
That’s why I reminisce about the days of NO MFING NAV APPS and Social Influencing MFers. You actually had to just get your azzzzszz out and Explore…
As always I’ve forgotten where I was going with this… but good luck and
HAVE FUN EXPLORING