First of all: WELCOME to the OSM community!
Great to have another hiker on board.
As I’m not that typical hiker, I can not help you so much with the hiking, but there are other users that have a lot more experience with it.
Maybe they can help.
There is a lot of information in the wikis about openstreetmap, but you are always welcome to ask in the board and I think everybody will be happy to help you in specific questions.
Have fun!