Thanks Cap'n! I'm moving again and actually made decent progress on Sunday (8/21). (My wife says if it takes more than six weeks, it's not a project, it's a hobby...)
I nailed up the drip-edge on all three sides and by the end of the day I shingled all the way up to the old shingles (about 9 courses, 14' wide), but I did not nail the last course in yet. I have shingled roofs before, but only about once every ten years; so I had to think long and hard about how to do this! I also forgot how easy it is to nail them, but cutting, carrying, hoisting, etc. is very tiring. This morning, I felt like I had played rugby. I'll post the pix of the drip edges and the unfinshed roof (as of 5 courses), but I'll end with my newest problem, and hence I need your advice again.
These first pix are of our famous end rafters with their drip-edges. This first one is the western most rafter. You'll see I reused the old drip-edge on the right side of the image running up the roof. This drip-edge used to be the one I (inadvisedly) pounded on to rid myself of ice dams. Because my new drip-edge does not have the same profile as my old ones, I had to use this old piece to mate-up with the old existing drip-edge coming down the gable. Wasn't sure how to join them in the corner, so I got a little creative... It worked out ok.

Then the eastern most rafter.
And from above (These side drip-edges have a lot more nails in them later on from the shingles) Note the mess up at the top of the image; stay tuned.

Here's the roof after five course. If you look closely, just underneath the gray tarp, you'll see the old shingles that I am advancing towards. Then if you look at the right side of the roof deck, you'll see that vertically, I lined the new shingles up with old ones, wich was easy to do. But horizontally, things won't be that nice. This was expected even before I got into this hobby.
Now here's one of the few problems I am running into:
As you can see, I have come up almost 50% out of alignment with the existing shingles. And there are no less then six layers of existing shingles in that valley at the top of the last image. Farther up the roof, this layer count drops to four.
Should I:
1. Go under ALL the existing shingles with the new ones (very ugly)
2. Go under ONLY the top layer of existing shingles (bumpy ugly)
3. Or both, i.e. put up multiple layers.
I am tempted to go with option #3. It was only three bundles to finish the first layer. And I now know exactly what my offset dimensions are. This would mean I would finish nailing down the final course at the top and at the edges, underneath all of the existing shingles. Then, starting at the bottom of the roof with the second layer; cut the first course of shingles almost in half *horizontally*, and advance on up placing the new ones under the first layer of old ones. Whatchya think?