Have you thought about insulating from inside?
It would be easier to repair your plaster walls than it would to repair the shingles.
Also, only small holes would have to be cut in order to blow the insulation into the wall cavities.

Here is a link that might be useful: There may be more answers here...

Hi - I just realized that maybe you mean the shingles are actually on the sides of the house vs just the roof, and if so, I would definitely speak the contractors and ask them how they would deal with it - they'll need to come out and see for themselves what things look like and then talk to you about possibilities.

I bought some new cement shingles that look exactly like the old ones on our house. I got them at a lumberyard, and I believe they were unmarked so I'm not sure who makes them. I see a company on the web called Weatherside that looks to be right. Color was not a problem as we were having the house painted. I do not know anything about construction, I was just thinking what you could do if a few got damaged. Good luck.

Thank you all for your assist. The shingles are on the side of the house so they would definitely have to go thru the outside. The inside walls are plaster, lathe and wallpapered. I guess that would be one reason to get everything done over!!! So that's the reason I would not have them work from the inside. Any contractor I have talked to say they will do there best but cannot guarantee anything. Yes, I did find those shingles listed on the internet. I would have to find out where they can be found around here and hopefully they would match the origals exactly. Unfortunately, they are not painted as the original ones were so matching a color may be difficult. Also, the finish on the shingles is a different, re satin finish, (the closest thing I can compare it to) sooo, replacing any of the shingles migt make it look a little mismatched. Is there any way to get a perfect match I wonder. Thank You

usually a hole is drilled from the exterior and insulation is blown thru this hole. holes may have to be drilled both high and about halfway down the wall for fireblocking.
once the wall cavity is filled a plastic cap is installed
and caulked. these caps can be painted over, but are not
too bad if not painted over (or at least imp..at least the wall is insulated)
when you call around to different companies ask what
they recommend.
best of luck!

I just recently had a few of my original asbestos shingles which were damaged replaced by the fiber cement shingles. They are not a perfect match, but they are close enough and when painted the same color you have to look for the differences.

I'm in the process of removing the asbestos shingles off of my 1875 Victorian. They're easy to remove and underneath were clapboards in pretty good shape but in need of painting. I used wood putty to fill in nail holes and any splits in the boards. I've painted about 2/3 of the back of the house, which is 3 stories. It looks awesome! The trimwork is so much nicer than being hidden by the shingles.

My dh insulated our house from the inside almost 30 yrs ago. He went through a lot of diamond drill bits cuz our plaster walls are like cement (2 part 1920s plaster). We had all painted walls at the time so that was different than trying to deal with wallpaper. Can some pieces of your woodwork be removed without damaging your wallpaper in order to drill behind them?
(Dh insulated from the inside in order to not damage our aluminum siding, and, by the way, we use very little oil compared to most people that we know.)
kathy