I did the Machame-Mweka route (up the Machame, down the Mweka) back in Aug 1999. Some of my thoughts:
The beginning of the trail from 6,000 ft up to the Machame Hut (10,000 ft) is pretty much a jungle. And when I was there it was a big mud pit. The Mweka was pretty much the same on the descent. I just had a pair of Rockports so I had to do a lot of routefinding on the way up to keep my shoes dry. Up I managed allright but going down..heh..heh.. I completely wiped out when the higher part of the trail disentegrated on me. The people with Boots/gaiters were just flying through this section. After I wiped out I was too. Just stomped right through the foot and a half of mud on the way down. No point in keeping the shoes dry anymore.
I descended the top part of the Marangu and yes it is very loose and with shoes you could gather a few pebbles in them. Again, I only descended this section and found it a lot easier to run down a few hundred yards, empty out the shoes, and repeat. Gaiters could have been handy. There was snow at the top but it was of no consequence.
The huts on this part of the mountain I wouldn’t exactly consider living quarters. All the porters huddle in them to stay warm and they’re so smokey from the fire you can’t even see the other side.
As far as what gear I took, I am probably not the best example. I had been traveling the world for 4 months prior and didn’t have any of my backpacking gear. All I had was a fleece vest, cheap windbreaker, poncho, WM Iroquos sleeping bag, and of course, the rockports. I did rent a cheap beanie, gloves, and insulating (ski) jacket out of Arusha. And, when I say cheap, I mean cheap.
But, either way, you’ll be much better equipped than the porters. They’ll be cruising by you bare footed with 50 lb loads on their heads and nothing but shreds of clothing. Of course, the higher level porters may have a shoddy adidas track suit as well.