A "simple" painting project which turned into reconstructing

It was time to repaint the house again, after a number of years. And as I got to the bulkhead basement access, I noted that a number of shingles were crumbling and rotting. So I now had a reshingling project on my hands. After a quick trip to a local home building center, I decided that level of home repair project was something I was capable of doing myself.
Little did I know...
I did decide that I ought to document the process (partly to ensure that I could put it back together correctly)
Before starting to remove anything
Note discoloration (accumulated crud) in the door joint on the left
Removing the old shingles and pulling all of the nails out
And taking off the flashing from the peak. At this point, it looks like there is some rot on the left side
Uh, oh. A HUGE carpenter ant. Reflexivly squished with a hammer. Almost 3/4" in length.
The peak there was thoroughly rotted, which is where the ant was living.
Well, at least one mistake when it was being built. The tar paper was laid down vertically, which means that moisture could get in and stay in.
After getting all of the shingles off of the right half
All shingles off; Now to start taking off the tar paper
And see how pervasive the rot actually is
It's bad. And affects some of the structural supports. This needs to be protected by a tarp to keep the rain out of the basement.
The foot of the roof is in really bad shape.
And at the peak. This level of repair/rebuild is waay beyond my skills. Time for a pro.
At about the one hour mark: the entire roof is pulled off. In amongst the junk, there was a moldy dessicated frog. It's the white blotch on the rectangular bit of junk at almost the center of the photo.
About 2 hours into the effort
About 3 hours into it, the framing is done.
And the new plywood is in place
Newly framed, using pressure treated wood for the contact point with the cinderblocks.
Inside, at the top of the roof, just below the flashing
Protective paper on, starting to shingle
At the end of day 1
Ok, this needs some explaining. In order to combat the problem of standing water inside the well, I got out the hammer-drill, and had put a few holes through the floor at low spots to help with drainage. The slab was about 4-6 inches thick. Except for the very last one.
It was only about an inch thick, hollow underneath, and the drill bit caught on a plastic bag, and was tough to pull out. Bizarre Why would there be a hollow with a plastic bag under it? After a couple of hours of thought, I could still not come up with a "normal" reason for someone to remove about 1'x2' of slab, put something in a plastic bag in that spot, and then redo the concrete. This, plus the context of having seen far too many tv shows about forensics, I decided that I really needed to call the local police department to ask for advice. They graciously sent an officer over. He pointed out that it was up to me, but that if I didn't open it up, it would bother me perpetually.
And the cause of all this? Plain old trash. The officer asked whether or not the previous owner was an older Italian man. He indicated that burying garbage seems to have been a common practice. Surprising question, but that was actually the case. Personally, I still don't understand the motivation to expend all that effort to bury a single trashbag of garbage vs. simply taking it to the curb for municipal pickup (or taking it to the town transfer station). Anyhow, the nice rectangular hole is now filled with gravel, and will provide good drainage.
Day 2, photos at about 1 hour intervals
New shingles almost completely in place
Now to frame the door
Note the angled piece of flashing to divert the rain
Everything done, now for cleanup
cleaned up (except for the old content)
And its finally repainted
Another view

Rebuilding done by Frechette Carpentry, of Natick Ma.

I absolutely recommend them. Very affordable price, and the quote included all materials.
Excellent craftsmanship. I will be a repeat customer. Contact information:
Matt Frechette
Phone: 508-320-0636