What questions should I ask the Roofing Contractor?

Get three written estimates.

Licensed in your state with insurance, also ask for references and check them out.

First of all, don’t tell the contractor that you need “a complete new roof”. If you don’t know your roof, then you don’t really know if you can re-shingle over the existing shingles (most roofs can use two layers of shingles before requiring them all to be stripped and replaced), and you don’t know if the sheathing needs to be replaced or not.

All you know for certain is that “you have a problem”, and you should tell the roofing contractor what your problem is, and let him estimate what it will take to fix that. He will probably recommend re-shingling the entire roof (probably over the existing single layer of shingles). Let him tell you what he recommends.

If you know the age of the house (and more importantly, the age of the roof, if it has been redone in the past), then you should pass that on to him.

When he gives you his estimate, then you can ask him:
1. What is the current condition of my roof, structurally?

2. If the estimate doesn’t say this (it should): Do you propose to use flat or “architectural” shingles? (I’m presuming that you’ll be using some kind of asphalt composite shingle, not a tile, slate or cedar shake shingle, and a pitched roof, not flat.)

3. Will you take out a building permit, or should I?

4. When you get ready to sign an agreement: Please give me a copy of your insurance certificate and contractor’s license (assuming you live in an area where these things are required for contractors – and even if they’re not legal requirements, you want to be sure that he has insurance).

I’ve had to do the new roof thing for three different houses. ugh
So many things…
How many roofs are there already? I mean layers of shingles. Some areas require that you can’t put more than three layers before ripping all off and starting over.
How old is the house? for example, my house was built in 1920 and the base for the roof was not ply, so it was more expensive to do the full tear-off and replace, but ultimately the best plan.
When I need a new roof, I drive around similar neighborhoods and look to see whose getting one. I’ll ask the homeowners (if I happen to see them) if they’re satisfied so far with the work. I look to see that the roofers have cleaned up. Talk to your neighbors and friends.
Call the better business bureau.
never hire someone who is going door to door unless you recognize the name of the company. Even then, be wary. Don’t necessarily go lowest bid, getting tires repaired a dozen times because they didn’t bother to clean up properly can eat up the difference.
What @WasCy and @Tropical Willie said. Keep in mind that the contractor is likely to get the permit much more easily than the homeowner.
Have a load of fun with this! ~

To add to @WasCy ‘s excellent post-

Also inquire about the flashing that will be used, and what the condition of your current flashing is. Improper flashing is one of the biggest causes of leaks.

Check with the Better Business Bureau and your state’s Contractor Licensing Bureau to make sure that the contractor has had no complaints.

Well… not to throw a wet blanket on the BBB, but nearly any contractor (or any other business, for that matter) that actually does business will have some complaints on file. What you really want to see with the BBB is that they respond reasonably promptly and properly to valid complaints, and that they handle them in a generally satisfactory manner.

@WasCy You are right. I started to write about complaint resolution, and then decided it was enough just to mention the place to search.

Do check http://www.ripoffreport.com/ They offer an interesting view of companies from the consumer’s point of view. They also allow the company to give rebuttals. You can learn a great deal from reading these entries, and sometimes you can be warned off of a bad company you were thinking of using!