"Underdiscussed (for me) is trail debris. The high Sierra, my typical hiking ground, is usually sand and gravel and I've learned too much dirt and gravel in my shoes chews up my feet."

Another issue that seems to vary by the individual. I rarely wear shorts when hiking, preferring to protect my legs from brush and sun with long pants. My trouser legs are long enough that they typically cover my shoes, and the result is that I rarely get debris into my shoes. I like not having gaiters because this also keeps my lower extremities cooler, and is one less disincentive to take my shoes off and let my socks dry out a bit at breaks.

I'm NOT saying that Rick is 'wrong' here. Just that a different solution is right for me!

"The bad news: find something you love and it will be gone/overhauled the next season. Rinse, repeat."

And isn't that the unhappy truth. The shoe I used to love changed on me, the 'last' (the underlying shape that the shoe is designed around) was made a little narrower so that it no longer worked for me. I've been fortunate in that my new favorite --- ASICS Gel Kahana --- not only comes in 4E width but doesn't seem to change much from year to year (even though the model number keeps going up by one each year).
What I do is to buy a pair of the 'new' model, wait for a chance to do a lot of contiguous miles in them (50 or more miles is best), then when I've confirmed they still work for me, I watch prices and then buy at least five pairs. But don't wait and watch too long, as by the time they're going on deeper discount sales, the size I want is likely to be harder to find in stock.
Then in a couple of years, do it again. PITA, but still for me, this is way way better than wearing boots.
Brian Lewis