Just started a Rags to Riches sim yesterday, using the rules found at
ModTheSims. I started in winter and had no problem. Wearing the right clothes was all it took to avoid freezing, even in the coldest weather, and my Sim spent most of the first week in the library anyway. He was using the library's computers to earn money by programming (Hack, Make Plugin) and writing.
Dylan (my Sim) did spend a couple days at Granite Falls, using the chessboard and woodworking table at the national park to learn logic and handiness. He also bought a tent from the ranger shack as soon as he arrived in camp. He started out making statues which I could sell from his personal inventory, then moved on to furniture which had to be sold from the household inventory after he got back home. I still haven't placed anything on his lot, which is one of the rules for the challenge I'm following until I complete certain requirements, so he hasn't spent more than a few minutes at home to pay his bills and publish his first 5 books.