Without meaning to criticize too much, all of your questions can be answered in one short answer-
"it depends."

Fitness-depends on how fit you are now and how much you will be carrying. If you aren't fit enough to walk ten miles a day with a pack now, start with some short walks fully loaded and see how you feel; keep it up until your hike.

Food-whatever you like that is light to carry and filling-look through the Food forum

Boots-whatever you can find that fits and fits your budget-there are dozens of them available.

Raingear-depends on the weather. Ask someone who has done that hike in the past what the weather could be like. I use real rain gear.

Plan for the worst weather possible, not the best. If your hike is 32 miles, you could be 16 miles from safety if the weather packs up.

If you are with 4 other beginners, make sure your companions are prepared. If they aren't, a problem for them becomes a problem for you.

Make sure you have enough fuel, at least two stoves, appropriate shelter for the weather, appropiate temp rated sleeping bag, map, compass or GPS-and the other "ten essentials."

Whatever you take, make sure you know how to use it before you go. Practice setting up your shelter, using the stove, using the GPS or compass, etc.

With that many people, I would get them altogether and do a gear check the weekend before you go and plan your meals so no one is short anything, including food. I would insist on this.

Remember-
"Adventure is just bad planning." — Roald Amundsen (1872—1928).

"Having an adventure shows that someone is incompetent, that something has gone wrong. An adventure is interesting enough — in retrospect. Especially to the person who didn't have it." — Vilhjalmur Stefansson, My Life with the Esquimo.