How much do the short term repairs cost? I would be afraid that if you wait to replace it will cost more because you may have roof decking that will get compromised by waiting.

I am getting quotes for full roof and for replacing the caps (which would require all of them replaced), and for whatever can be patched/fixed.

Not going to wait, I agree it could end up costing more.

I am concerned about getting the current roof repaired as this will still be costly, I will probably need another roof in 2-5 years anyway, and there might be damage underneath that I cannot see now and will only get worse.

So, while my current thinking is to go with a new roof, I am no expert and want to make sure I am doing the right thing.

Also, want to add - there is about 3000 sq ft of roof, with a complex roof line, with three peaks that have 90 deg angles on the top (45 deg slopes), so I am not looking forward to the quotes.

Yeah it's scary how much more anything over a simple two plane roof is. My home has the garage roof and house separate roofs and different directions, plus a smallish bump out roof section. The cost was at least 1/3 or more over my parents house with 2 simple plains (not sure of correct terminology), same shingles, same roofing company and their square footage is about 1/3 more.

The roofing company, a good one may be able to help with ideas for preventing future ice dams. More venting and attic insulation suggestions.

New roofs are expensive. However, fixing damage to the structure caused by a slowly leaking roof plus then putting on a new roof is even more expensive. To me, that does not look like a 25 year roof, and it also looks like the roofers didn't send their A-team to install it Based on those photos, I think you should reconcile yourself to biting the bullet and getting a new roof put on now.

One look at your pictures, would have me contacting a roofer and getting a new roof, asap. That roof is in terrible condition. I have seen roofs replaced, because they needed it, but, never seen one in as bad a condition as yours.

Thanks to all who commented. The pics here show the bad parts, rest of roof looks ok for an 18 yr old roof. The damage was due to people walking on top of the caps swinging pick axes to get ice off.

I am getting quotes, and will likely get a new roof, but my bigger issue is finding a roofer I can trust. So far, only one out of four that have looked at the roof has given me estimates for repair and replace, and several others who said they would come by cancelled and never rescheduled.

It's more a case of when you need a new roof rather than if you need a new roof. If it's 18 years old and you put money into repairs, it merely gives you a little more time.

Several years ago we replaced a roof that was near the end, but had some life left. Inquire with the roofer who gave you a quote to determine if there's a busier/slower season for them. That could explain your lack of bid responses. I'm in Florida so we can work year-round but when we had our roof done, a crew removed and did the membrane, then a single worker installed the entire metal roof. A few months later, their backlog must have eased and the same company did my neighbor's roof in about three days. It doesn't hurt to remind a company that you're waiting for a bid. Consider that many people get multiple bids so companies might have a 25% to 33% success rate. A friendly reminder indicates you're serious and sends a positive message.

We had a similar experience with quotes. One company sent a well presented proposal with options. One sent a bid rife with grammatical errors, for the wrong material. The other sent a decent bid, again with the wrong material, and said he didn't install the product we wanted because it was too difficult. After one bid and two misfires, hurricane season was approaching and we had money in the bank so we pulled the trigger and were quite pleased to have it behind us.