Roof leak. Three contractors, three diagnoses, three estimates. How do I know what to believe?

[Johnhw2]

Roof leaks are hard to assess. Yet all three had a fix. I'd get a fourth opinion. If he says not sure but costs x or x per hour to find out go with him or who first says it.

[johngolf]

Originally Posted by Listener2307

How would I handle it!?

I would call repairman #1 and ask him to fix the flashing. $300.
When he shows up, verify that he is there to fix the flashing, but ask him to look around while he's up there and see if he can find another problem. Offer him a cup of coffee, and ask him about his family and business.

If the roof leaks again, I would call this guy with whom I carefully crafted rapport and see if he would like to take another look. If you have done a good job of establishing yourself he'll come back.
If he refuses, then on to candidate #2.

Sound advice.

[karen_in_nh_2012]

Originally Posted by johngolf

Sound advice.

OP posted a year and a half ago ... hopefully his leak has been fixed!!

[kitty61]

If you don't have a chimney cover or it is rusted out and the water has been leaking every time it rains it is likely the metal chimney stack is rusted out and the chimney insulation is damaged. Dangerous not to replace it. The only way you are going to know is by digging in and exposing it. You will be able to tell right away just by looking at the chimney stack.
If your chimney is brick with a metal stack the water is also going to break down the mortar of the brick and that will also need to be repaired.
https://www.highschimney.com/reasons-chimney-leaks/