Well I found out the hard way that Lowes no longer stocks the Hardiplank I was going to use. So I can either order and wait... or do all of the siding with the leftover shakes from the house. Though that will take longer to do than throwing up clapboard siding, it will still look nice, not cost me a dime, and I won't have to worry about storing all these stinkin leftovers!
So that's the new plan. Meanwhile, the roof is all shaked now except for the ridge capping.
In you were wondering how I did the shaking at the pitch change, basically I kept hanging full shingles till the top course was installed for the lover section of roof. Then I just used a skill saw and ripped them down to the correct length in one shot. The biggest thing to watch out for is setting the depth of the saw blade, cause you don't want to cut the tar paper underneath. I set it a little shallow, then broke off the lower layer of shakes at the cut line.
Then I ran another starter course with an edge cut to a 45 degree angle to meet the lower line of shakes. The finish course goes on top and extends over the lower shakes about a half inch. Then you can continue on to the peak. There may be better ways to do this, but I coudn't find anything online and just went with the basic principles of shedding water. There shouldn't be any leaks.