I do roofing as part of my business. There is a wide range of immoral/unethical as well as salt of the earth people on both sides. If I find no damage I say so. If I find questionable damage I say so and let the homeowner decide if they would like to file a claim.
On steep and high roofs, most insurance adjusters don't want to get on the roof to inspect. They will either just total it so they don't have to get up there, or they will pretend to look either from the top of a ladder or with a drone and say there is no damage. I have had people call me because their roof was totalled by their insurance company even though they had no damage. I have also had customers with undeniable damage. The insurance company has hired a 3rd party inspection to determine if there is damage after fighting and saying their adjuster found nothing. It is rare that the 3rd party does not find the same damage that I have found. Also, having your roof replaced using your homeowners insurance is not free. You still have to cover the deductible.
There have been enough storms recently that some reinsurance companies are in bad shape. It is common for an adjuster to take bad measurements and miss things or even add things that aren't there. There is just a lot of incompetence all around.
Another favorite is when people have their agent come look. Some insurance companies pay agent bonuses based on claims. In other words, the less claims their clients file, the bigger the bonus. Of course, those with an off kilter moral compass don't find any reason to file a claim. This isn't tinfoil hat stuff. I did some remodel work for a guy that was an independent agent that told me this, and also one of the 3rd party inspectors that the insurance company hired told me that. I don't know that all insurance companies operate that way, but there are al least a few that do.
Ultimately, if the roofing guy seems like a sleazy salesman, run. If he seems like a straight shooter them let him help you. In my area, the residential reroofing business is a joke. Most companies send a crew that speaks zero English with no supervision. The salesperson shows up for the sale and to collect a check. The quality of work depends completely on the crew. No one wants to stick around to solve problems, do quality control, and make sure things don't get damaged. If you find a roofing company with a reputation of having a representative on site during the work, you are usually in pretty good hands.
Also, I forgot to add, never sign a contract with a roofing company before you have the damage appraisal from your insurance company. If the contractor sees things differently they can argue it with the insurance company and you will get an updated report. If someone is trying to get you to rush into something before you have things sorted out with the insurance company, they definitely are not in business to help customers.
