I agree with Brooke, it probably means "to turn out". Like in life, you eventually forget all the bad stuff and remember the good, the road sometimes turns out in a place you don't want it to, it lands well or not so well. I'd like to correct your title. You probably meant "can you help me understand". When you say "help me explain" it sounds as if you are explaining it to someone else and you need me to help you do that.

Land substitutes as a "to be" "You forget about the number of times the road (life maybe?) does not come out to be awkward and [you] remember the times it does." Does this help?

I'm a native English speaker, and I don't know what the sentence means. Maybe I need to see the map. That said, the word "land" as a verb means, "to come down to the ground/land". I could say, "This plane will land in one hour." I hope this helps! If it doesn't, please give me more information!