I've been thinking about doing that myself. The last time I shingled it was a few decades ago. It's time again, but the roof is more ready for it than I am.
I like chalklining the layout, to keep everything nice and straight. The last time, I had to substitute twine for the chalkline because it was getting too dark to see the lines otherwise.
It took a lot of shingles, and a lot of nails. At least I have enough nails left over from the last time. I had bought a fifty-pound box.
Kara and her hubby had to strip the roof down to the rafters in places, and replace a couple of those, then they had to put particle board on, then rain barrier, then whatever came next, then shingles. Some of the supporting joints (I forget what they are called) under the larger eaves had to be made because they were rotted out, so it has been a major undertaking.
They will not get finished before winter sets in in northern ID. I believe it is a three bedroom house, originally, with a basement, but it was built at a time when rooms were large so the house has quite a few square feet of roof to cover.
Last year, it was the foundation. Her husband works full time, so it has been a real challenge. She said they finally got rid of the construction dumpster in front of their house!
I kind of like helping local people who feed their families by doing that sort of thing to get another family-feeding job.
When I was younger, I liked to see the results of a job well done. Those were rarely DIY jobs.