I'll be spending part of my Sukkot in a medieval tent (our local chapter's event is this weekend, and I have to be there to work). Next year I plan on hosting the local Jewish potluck group at my house and I'll put up our tent. I plan on getting historic with it and put up a low table and pillows on the carpets so everyone can sit and recline on the ground, as was (and still is) typical among nomadic cultures. I need to do some research, but I would like to serve a historically-correct food as well (well, what they would have eaten once they got into the Promised Land and didn't eat manna anymore).
Being a re-enactor and history major, I've been scratching my head over the booth thing. How did that evolve? Is it a city's answer to pitching a tent when you have no ground on which to stake out a tent? Because I'm thinking if Hebrews were wandering around in a wilderness, there weren't a lot of trees and palm leaves. There were supposedly 600,000 Jewish men, so there would have been 600,000 dwellings big enough to hold a family. And unlike Sukkot booths, they had to be weather-proof, because people lived in them constantly. Any wilderness with that much in the way of resources doesn't sound like much of a wilderness to me.
It would seem more probable to me that they would have had cloth or hide tents (the description of the Tabernacle supports both theories), just as nomadic people in the middle east have always had. Your poles are used to make a travois behind your camel or ox or ass, and everything's wrapped up in the tent for safety and put on the travois. Voila, time to move house; no wheels or roads needed. And based on the time it took a nomadic Native American tribe to break camp, Jews in tents could probably be ready to go in 1-2 hours. The construction of the tabernacle is a lovely piece of engineering from the standpoint of a mobile building, and it could likewise be taken down by a team of people very quickly. All of those sockets that are mentioned are for making stable walls and--I suspect--for putting together two pieces of short wood (easy to pack) to make one long pole. Many re-enactors use a two-piece pole for their roof uprights and they have a metal sleeve that holds them together.