I think that there have been some really good points brought up here. I would like to add one more. Budget.
You can drop a hundred bucks on a pair of keens and get who knows how long out of them....
You can also drop 800 bucks on hand made cutsom fit stuff.
I tend to go for the middle ground. I used to make my living backpacking around. I have spent time on the AT, the CDT and all over the west coast.
Needless to say boots/ shoes are one of three things I dont skimp on when I play or work outside.
1. Boots.
2. Rain gear.
3. sun glasses
They are all just as important in my book.
I have has Vasque's Aslo's garmots scarpas la sportivas rocky's, lowes, chipppawas and a few more I am sure.
Here is what I have found out after the last 12- 15 years of many miles and hard use.
No one makes a boot like they used to unless you want to drop a huge chunk of change
my current go to is the asolo TPS line.
I have had 4 pairs of these over the last 6 years. I have used both the gore tex verson and currently have the non gore text pair.
These are hands done the most comfortable pair of boots out of the box that I have ever had, and with your use it sounds like you could get some really good use out of them.
The gor text version is a bit hot in the desert and they are a bit heavy for those 20+ mile days. With that being said they are a truely awesome boot and you would most likely love them. Toss the foot bed that comes with it since it like many these days is worthless. This of it like the tires that came stock on your rig. Cheap and crappy.
grab a pair of super feet and your feet will love you at the end of a long day.
If you are looking for something more light weight, check out La Sportiva's line of approach and hiking shoes. Super sticky rubber, very stout. Lots of people climb in them. I logged many a mile in the desert of south utah one summer. Only true problem is a bit of a tight toe box depending on fit.