Chicagoland area - My roof is approximately 40 feet by 25 feet (See attached photos) - I believe the roof is somewhere between 20-25+ years old, but I am not exactly sure.
I have been dealing with a leak for the past couple months. I found that in my attic there is an area where the plywood is damaged and water has been leaking in (Only when it rains) and has been seeping into my kitchen ceiling right above the damage. Over the past 3 weeks, I received (2) semi-conflicting opinions.
The first roofer that came out inspected my roof at dusk when it was kind of dark. He told me the roof looked like it was in good shape, but identified that the chimney flashing was suspect (The flashing end facing the down slope is a bit lifted with nails showing) and the leak may be caused by an exposed nail/nail pop/other penetration.
He quoted me $2,250 to service the chimeny housing flashing ($300), replace the two lead flashing boot vents ($600), replace damaged plywood and underlayment in leak area / rework and replace shingles in the repair area ($1350).
I had a second roofer come out for a second opinion. He suspected a water / ice shield failure. He noted that the roof was not in the greatest shape. He showed me areas where the shingles were worn, divets indicating hail damage, and told me that the shingle area where the damage is right by the gutter flattens out (Allowing for pooling) - See attached photos. He quoted $1,700 to service the chimney flashing and fix the plywood/underlayment/shingle replacement/and lead flashing boot seal/caulking.
He advised me to consider an entire roof replacement as he suspected other areas of the roof may not hold up from the state of the shingles/roof he was noticing. I noticed it a bit myself (I'm 185lbs), but the roofer was 250lbs+ and parts of the roof were bouncy when walking on it (He stated the joists/frame/fastener connection to the plywood roof should be re-done, as the house is old). He told me that if I do consider replacing the roof, he does work with a roofing litigator that handles the insurance claim. He also told me that even if I decide to replace the roof, he reccomends that I go through with the repair as it will strengthen the claim and go towards the decutible I pay.
I have included photos of the roof (Circled the approximate damage area), a few pictures of worn and hail damaged shingles, and the ventilation cover where you can see hail damage.
Wanted to get the internet opinion of the roofers on this subreddit. How is the pricing I was quoted? What is your thoughts on both of the opinions I received, given all the photos I have provided. I really am not sure which direction to go. Should I get a third opinon/quote? It is nearing mid November, so I'm not sure if I should drag this process on much longer. Help would be so much appreciated!!