If I'd go serious distances through difficult terrain and possible adverse weather, I'd take a whole other approach, but since I'm not even a beginner, that's not what I should be focusing on right now.
Therefore, I'm doing the above, or "easy-mode" first, partly for the reasons you mentioned as well.
I need a plan though. That just a personal quirk.
Professional guides will often do day-by-day plans outlining what you expect to accomplish on each day and where you expect to be. Each day is the associated with a given amount of supplies (mainly food).
Just go through it, add it all up, and pack it!
Last time I did a reasonable serious trip I was in the Drakensburg mountains in South Africa. I just figured out where I was hopefully going to stay each night, and then laid out my food on the floor of the hotel to figure out what I needed each day. I also planned for a shorter route I could take to leave early.
In the end I wasn't feeling so great and ate a lot less food than I brought... Fortunately I'm fat, so I've got plenty extra. 😂 (Seriously, pretty much everyone who isn't a cancer patient has at least a week or two worth of calories stored as fat!)
I also ended up using my backup plan, as I lost a day due to being unable to find enough water in one spot. So I spent a night somewhere I wasn't intending to that did have water, and made up for it by hiking out a shorter route with one less night spent somewhere else.
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Yeah, that's why I'd like to roll with a set plan from the start... It'll spare me unnecessary headaches, maybe not all, but most.
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