Very cool house! Interesting meshing of older construction methods with "modern" design. I have a 60's modern house (built 1960) that we're slowly revamping as well. Some of the stuff they did back then made sense. Some of it didn't. Materials for construction didn't have the longevity for some of the design aspects that were dreamed back then.
I notice you have a flat roof.... is it tar/gravel or has it been updated? Ours had a tar and gravel (2nd iteration that was installed in the early mid 80's) that we had torn off and replaced with a modern TPO setup instead. The tear off/removal costs were insane because of the cost of disposal of that tar/gravel mix.
We were going to replace the roof first since we thought it would be best to get the structure watertight from above. I'm not certain if the roof is original but I know it is not tar and gravel. We received a quote to install a new roof and it was pretty reasonable (under 10k and they were not going to remove the material which sort of looks life a very stiff foam).
However, we looked at 3rd floor ceilings and walls and did not find a drop of moisture so we were pretty certain the roof was in decent shape. Plus, I was interested in removing oil fired furnace, moving the wood burning stove and making other changes where would possibly need to add/subtract holes from roof.
And then I got involved with demo and then found rotted beams and added windows and promptly forgot entirely about that darn roof for like a full 2 years. That is until I climbed up there and found this surprise (pictures). I'm embarrassed about this (pro tip: clean your gutters).
The roof is drained using two low spots that feed a pipe that exits at the top of the roof. They are covered with a screen that is held down with bricks. Nobody (who will remain anonymous) checked the drains for 2 years. The grills were clogged with leaves but I think the glass half full story here is I now know for certain the roof does not leak since again we have found no water signs on interior.
The first two pics are from late summer when I found the worlds best birdbath. The last picture was taken during fall cleanup and you can see drain in lower left corner.
But let me say again - clean your gutters!
BTW - you definitely get it with 60's modern houses - some of it makes sense and some not so much. Onward, upward, better!
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Holy ****! Is the ceiling in the kitchen like the pics with the big beams?