The siding is fiber cement board. Both James Hardie and Certainteed make the product. It can be bought and installed primed or prefinished. The prefinished has I believe a 30 yr product warranty, 15 yr finish. I bought mine primed, put one color coat on before installation and 2 finish coats after it was up. Unlike wood products the fiber board does not absorb moisture so the paint does not peel. The factory prefinish is recommended because it is applied and baked under controlled conditions. The down side is it will require touch up from handling during installation (nick and scratches), you pick from their colors and it's 1/3 more in price. They also offer a full trim line made from the same material. It's heavy, expensive, tough to work with, but when its done correctly it's bulletproof (not literally). There are more and more accesories avaible today for this product than just 10 years ago. Go to the James Hardie web site for all the info.
I would do the roof first. Start from the top and work your way down.
Actually roofs and siding are installed from the bottom up (you get what I mean).
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