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I don’t think I will go that far for my first trip, but those knowledge are well needed.
I am somewhat in shape, but in a different way. I am more used to high tenacity short to mid duration workouts. I have been on few hunting trips with backpacks it’s a complete different type of workout for sure.
Consider I am taking my wife and my dog with me, I will probably end up carrying most if not all their stuff. Weight will matter a lot.
 
I didn’t link to a book, I linked to a short article.

(Here is the link to his book from the article you cite).

To help select your gear, I recommend my book, The Ultimate Hiker’s Gear Guide.

Its not any issue to start small, but the point I was making is that skurka is going to give you a very comprehensive and professional view which is going to be overkill unless you are reading him with a "grain of salt".

For example, when I completed the 6,875-mile Great Western Loop in 7 months (33 miles per day pace), I carried lightweight gear and calorically dense food, and hiked efficiently by always taking care of my feet and avoiding navigational mistakes.

This is the stuff skurka is really an expert at talking about.
 
Consider I am taking my wife and my dog with me, I will probably end up carrying most if not all their stuff. Weight will matter a lot.

This is a good point to be self-aware of. I would actually weigh your pack(s) before you go.

Good to set a sanity limit on your personal pack around max 40 pounds. Hers probably 25-30. Fully loaded.
Those weights are fine (short distance) and often attainable without buying new gear.

The cheapest and lightest gear is the ones you take out of your bag and leave at home (and/or never buy).
This is a key takeaway from skurka as well. :D
 
My favorite pieces of gear. Tarp tent when there is no bugs saves a ton of weight. I got a coupler that holds two thermarest self inflating sleeping pads together. Also a wedge piece that zips into a mummy bag to make it work for two. The bag is rated 0 degrees and the wedge is rated 40. That way you can change the temp rating by flipping the bag. A single trip can feature drastically different sleeping temps depending on altitude. A down vest or sweater makes for a great pillow that is immediately at hand for bathroom breaks at night.
 
Quick update, I went to REI this morning and signed up for a try up appointment next week to go try on all the gears. I tried a few backpacks and I like the Gregory Baltoro 65 the most so far.
 
I don’t have anything to add that hasn’t already been said. You’ve been given great advice so far. Like any hobby, the rabbit hole is endless.

The gal and I both have professions that require us to more or less be connected at all hours of the day. We get out to the boundary waters in northern MN several times a year with our blue heeler and just disconnect from everything. It feels great.
 
People often get lost or injured hiking in Hawaii. Some think they are going on a short hike & go missing.

Bring a phone with a portable solar charger. Let people know your plans in advance.
 
I may be late to the party but from a person who use to be a air force cadet ;)

Its always good to know your local fire regulations and how to create fires safely because you may not want to light a fire now but when you get out there you may change your mind. Just like how I always change my mind going down to the shops and I end up buying that whiskey I've been thinking about ;) And remember to pack real food, none of that McDonalds wannabe stuff, something that will keep you full and full of energy for the day.
 
People often get lost or injured hiking in Hawaii. Some think they are going on a short hike & go missing.

Bring a phone with a portable solar charger. Let people know your plans in advance.
Keith, good point I am following the same process as if I am going out on hunting trip, let close friends know where we are going, what path, when to expect us to be back and emergency contact solutions.
 
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