It is a bit unclear whether you'll be taking trails, roads or some combo of the two. It matters. If you come back here to read the answers to your post, give us a few more clues about your plans, ok?

Judging by the gear you mentioned, I'd venture to say you are making it up as you go along, using only the available store of knowledge you already have in your head. There's nothing wrong with that approach, except it forces you to make more mistakes than are really necessary.

OTOH, a lesson from painful experience usually "takes" better and lasts longer than if someone just tells you what to do. If pain's what you want, your current approach can probably provide you with enough to be memorable.