For the cedar shingles, I've done a lot of that over the years. It's best to use a nail with a large flat head. This means you likely can't find ones that will fit in an air nailer that are suitable. Sorry, but for this job, you can't beat a good old fashioned hammer. I've watched contractors use air nailers and it seems they spend more time fidgeting with the pressure so as to not split the shingles, than actually shingling. On the plus side though, you will have lots of split kindling lying around for campfires.
At many points, like on the top couple of rows or when you come up to windows and things, you will be faced with making a number of smaller shingles. Traditionally, you measure then score it with a very sharp knife and snap it in two. This takes practice but you will quickly get the hang of it. Thinner sections will easily cut straight through.
However, a good that hint I will pass on is that if you happen to be able to keep a portable table saw handy then you can speed this up a lot. Measure one, use it to set the fence on the table saw and then you can cut a bunch exactly the same length with little effort. Just don't cut too many at a time. Things are rarely as square as you would think and so you may need to adjust the length now and then. I also waste less shingles this way because I have not perfected the score and snap like the 'old folks'.
My last bit of advice, spend a bit extra on a good, comfortable nail pouch. You will be wearing it a LOT.
Easy work but long and repetitive. However, in my opinion, you can't beat the comforting look of a cedar shingled home.
