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5 estimates? Why 5? Why would you do that to yourself? Normally if you are dealing with reputable companies you don't need more than 2 estimates. I advocate to people to always get at least two estimates and if the roofers are saying something very different or if the roofers are way way way off in price, get an equalizer, get a 3rd. Obviously if you don't trust a roofer disqualify that roofer immediately. I beliee you have now fallen into "Analysis Paralysis" which is what happens when you have too many opions.
But back to the topic, I said you are focusing on the wrong thing. Why did I say that? Because you can take the best shingle in the world and if installed wrong is compeltely garbage. i can take the worst shingle, known to fail, and if installed properly will last some ammount of time. So you should focus on the roofer, not the product. The roofer is more important and a good quality roofer will only want to install good quality product.
The roof is a system comprised of many components, not just the shingles. You have the water proofing underlayment such as ice shield, the water resistant underlayments such as felt. You have the shingles, the ventilation and the flashing details. All of these things add up to equal one roof. Neglect one and your roof is doomed to fail.
But the roof is more than just product it is detail, know how and heart. Heart? yes heart. It takes the utmost CARING the utmost DESIRE to want to install a good roof. It's hard work and easy to fall into the train of thought as to do what's easier, instead of what's faster. Faster and easier seldom ever equals better. At the end of the day you ened a roofer that cares about your roof.
So what product is best? That's hard to say. Each manufacturer has multiple plants and it seems each plant puts out varying levels of quality. I will tell you in my area Atlast is known as a cheap commodity shingle. I have Tamko Heritage on my house but I stopped using it because I was having seal failue issues and at the time they offered no contractor certification program, but I hear they started up one. Ownes corning is a decent product backed by a great company. I don't install very many OC's though. I primarily install CertainTeed Landmark shingles and my feeling is that they are the best on the market in my area. I'm sure others will disagree with me.
But don't miss the point, the roofer is more important than the shingle.
Any roofer worth using should be able to do the roof with NO MONEY DOWN.
The only scenario I would ask for a deposit is on a crazy odd ball shingle that had to be special ordered.
As a certified and licensed roofing contractor, my reputation is on the line. I debate this topic quite often with other roofing contractors who seem to care more about profit than a job well done. Well, I can tell you from past experience having been a professional roofer for 14 years as of the time of this posting, that the chance for failure increases exponentionally when installed below freezing. It's better just not to risk it.
Personally I will not, unless absolutely necessary and the customer signs a disclaimer of limited liability, install a roof below freezing and really really want to install the roof at 40 or above. The shingles need to seal, and will not seal unless they warm to about 70 degrees F ambient temprature. This does not mean it needs to be 70 outside, because the shingles will warm from the sun.
So what can be done to install the roof below freezing? Well first, the roof should not be gun nailed below freezing. This is because the shingles become brittle and it's easier to "blow through" with your nails. It's also harder to regulate air pressure when it is cold, I speculate because of barometric pressures, but I am just guessing. Therefore the roof should be hand nailed. This takes more time. Furthermore since the seal strips will not seal, they must be manually sealed with proper compatible adhesives. This will also take more time, and more material. I once spoke with a roofer in Alaska who builds tents around the houses he is working on and covers them with tarps and heats with propane heaters. Now that takes real time! The question is, are you prepared to pay for this extra time? Can you wait a few more weeks?