In 2003 and 2004 I reroofed my house and garage. (I took a break during the winter!) I used rubber slates like TOH used on the Billerica house but I went with a different manufacturer. I chose this product because I'd lost two asphalt shingle roofs to hail damage in 3 years and the rubber slates are basically hail proof. I had one helper. We did all the work ourselves mostly on weekends) and it was a BIG job. My roof is 10/12 pitch, two stories, about 40 squares, and has a lot of intersecting roof lines and dormers.
I have two favorite stories about this project. One involves my coworkers. I live close to where I work and some of my coworkers are also my neighbors. One of my neighbors/coworkers (R.) passed my house every day on the way to work. R. was asking me about the roof project one day when I came into work. Another coworker (T.) overheard this and asked me about it. I told him I was reroofing my house. He asked me a few questions about it -- size, pitch, two story house, etc. Then he looked at me and said, "Nah," and smiled and shook his head. He thought I was making the whole thing up. He apparently didn't think a woman would roof her house herself. Then R. told him that I really was roofing my house myself -- he'd seen it. Then T. looked at me in amazement and said, "I'm impressed!" He went around work telling people that I was roofing my house myself.
My other favorite story is about my non-dumpster. I knew this project was going to be long since we were working on it in sections and mostly just on weekends and I didn't want a dumpster for months. I had intended to collect up all the debris from the roofing project (including tearing off the old roof) and then get a dumpster when I was all done to get rid of the debris. Shortly into the project I decided to start getting rid of some of the debris in my weekly garbage. I figured that every little bit I threw away during the project was that much less I'd have to shovel into the dumpster at the end. Well, since my project took a long time I ended up throwing away my whole entire old roof and all my construction debris in my weekly garbage.