Guy 3 will not be in business for long at those rates. Guy two by far has the best scope description and thought process in my opinion. As long as you have vetted him and check his license (if required in your area), insurance and references he would be my guy. And they will tell you soon enough of the squirrel needs to be professionally removed.

Thanks for the response. #2 is a solid company. I’ve tried to hire them in the past but they stay busy so the wait time was long.

Each of 3 are doing different things so the question you should ask YOURSELF is what needs to be done. #3 is installing drip edge and fixing squirrel hole which is all you've told us is needed. Do you KNOW that facia is badly deteriorated behind gutter? How long has gutters been on house without painting behind them? How long has roof been on house? Slate isn't something I know about but all I've seen lasts as long as building. Do you anticipate replacing entire roof within next 10 years? Are leaks visiable inside building? If not,why is the ice and water barrier being installed? I get the feeling slate doesn't need drip edge as installed on your house or there is drip edge that is inadequate which can be rectified with counterflashing.

Thanks Klem1. Water is leaking behind the gutters on the front and back of the house. The gutters have been cleaned, so they are not clogged. There is evidence of water leaking along the back wall. I had the gutters replaced about 12 years ago which seems to be when the problems started. I called the installer back a couple of times.

I have read as well that you dont need drip edge with slate but not sure how to fix the issue beyond getting gutters reinstalled or replaced. my neighbor has the same house build and looking over at her house during rain storm I see the same problem with water going behind the gutters on the front of the house. We did not use the same company for gutters.

About the fascia I dont know. Initially I had a pest/wildlife guy come to get the squirrel out. He said there was wood damage and i needed repairs beyond his scope of work. He took photos and there is water damaged wood.

I do not plan to replace the roof in the next 10 years though I have gotten one estimates to see if it made sense to repair versus replace. I had flashing around dormers replaced two or three years ago, which was another big bill. There was a leak.

House was built in 1951. One of the roofers said the slate may be good but the underlayment deteriorates.

Open to all recommendations.

Recommendations for your circumstances is impossible to make long distance. As witnessed by 3 contractors recommending 3 different solutions, how could I nail it down having never inspected the place? The only POSSABILITY I might suggest investigating is counterflashing that can be installed quite simply. How bout going with #3 and seeing if that stops water going behind gutters if that's your biggest complaint? It's possible that flashing was in place until gutters were replaced and flashing was left off.