As others have said, we all were rookies once. Few folks join AMC pay their $$$ for guided hikes & take the skills course before they do one hike.
Hopefully they learn some lessons not far from the road. My first two winters were spent in cotton, but only on good days & in Southern New England, working my way up the 3rd year sith better gear & some lessons before getting to the Whites. People without headlamps, hopefully they get within a few 100 yards of their car before it gets too dark.
Footwear is a tough thing to grade. most of us start in what we own. (I did Greylock, Mansfield (2x, once to the nose) & Katahdin in old 3/4 high Raquetball sneakers. My feet were fine, in ME, I learned I needed a shoe designed for hiking. The strongest hikers can get away with weaker shoes since their feet are trail hardened, look how many people where trail runners now. Through injuries I've been from sneakers to big backpacking boots for summer day-hikes & now am back in trail shoes. I do believe in the past year or two I did go up Monadnock in running shoes, starting at 4:00 PM & with just a small fanny pack. - had light.
On my first Camel's Hump trip I came across obvious tourist in sandals & speaking with an accent. We were going up a 4K peak in New England, did they bite off more than they could chew. Once we learned they spent most summers in the Austrian Alps, we figured Camel's Hump was a quick little walk for them.