It is not unusual for me to be $2,000 higher than my average competitor. Infact I have come to expect that unless I am bidding against one of the larger companies, I will probably be $2,000 higher on the average sized ranch type house. But I promise I am doing $2,000 more worth of work. You have to forget the price, the price is the LAST thing you should look at. First, quality of materials and scope of work will dictate price!
I haven't seen these proposals so I can't point out the differences, but if it is not in writing it does not existing, meaning you have one proposal not three. Put them side by side. I will mention what differences my proposals have versus my competitors;
Protections, we do alot to protect the house. It makes the clean up alot easier. Ask your neighbors and friends who have gotten new roofs. The #1 complaint is dirty dirty dirty. Not our jobs, this costs money.
Old roofing nails removed and wood nails resecured. We call this tuning up the roof. Bad things can happen going over old nails. This takes a little extra time and time is money, but you get a better job. Of course we replace rotten wood, but that is an extra indicated on the proposal. FWIW, we charge more than your friend Gary does for rotten wood.
Ice shield, 6' at the gutter lines is pretty much our norm because I actually understand the code. However most guys will install 3' and get away with it. Furthermore we install ice shield in valleys, and pre-flash all areas like chimneys, skylights, pipes, walls, etc... with ice shield. You may be thinking you have no ice so what's the purpose of ice shield. These are the areas most prone to leakage so a little extra insurance is a good thing.
Felt. Most guys use 15, the minimum allowed by code. We used to use 30 Lb, and have since switched to the fiberglass reinforced felt paper. It lays smoother and qualify the customer for extended manufacturer warranty's (which I will discuss later).
Starters, we install a good quality starter. Not only at the bottom edge of the roof, but bleeder courses at the gables/rakes. Extra time extra material = extra money but also extra wind resistance for the customer.
Shingles, well there is some chit on the market that we have previously discussed. Sounds like Gary is using a good product. I'm not too familiar with OC really, we only install it upon request, but it sounds like he's using their upgraded shingle which will cost more.
Hip and ridge shingles, we use manufacturer matching starter shingles, no longer do we cut our hip and ridge from 3 tab. Not only will the hips wear away faster but they don't always match perfectly in color and then your roof looks like shat.
Ventilation, most guys repeat the mistakes of the previous roofer. We make sure that there is adequate ventilation. The installation of a few extra vents, which is required in most cases, costs a few extra bucks. But this is the difference between having a manufacturer warranty and not. It is the difference between mold in your attic or not. And in my area also affects various ice concerns such as ice damning and frozen attic condensation.
Flashings are critical to the roof. Many many guys will simply re-use old flashings or even slap them with roofing cement. We replace all old flashings as possible, 99% of the time the flashings gotta go. Not only that, but proper installation of counter flashing seems to be a lost art. We will properly step and raggle our brick counter flashing. Not only does replacing the flashing take time and material, but doing it the right way take more time, time is money. But this is what determines if your roof leaks in 5 years or 20 years. Big difference?
Clean up, because we pride ourselves on the clean up of our jobs (remember the protection) we take a little extra longer than most others with the cleanup.
Modified bitumen, as you said there is a section of flat roof. I would be installing a 3 or 4 ply modified bitumen 20-year rated system. Some guys would install a 2 or even one ply 10 year rated system. This doesn't make sense to me to install a 10 year rated flat roof with a potentially 30 year shingle roof. Does that make sense to anyone else? Also what edge metal and flashings are included, because for me I would have a metal flashing at all outside edges. Learn more about modified bitumen here:
http://reliableamerican.us/services/...ng.html#ModBit
Warranty, I include a manufacturer 25 year workmanship guarantee on all my shingle roofs. This varies in price based on the size of the job, but certainly is a minimum of a few hundred bucks. If the customers opts not to have the CertainTeed 5 star warranty, we will stand behind the shingle roof for 10 years. 5 years is the norm. Some guys may be offering 1 or 2 years, the minimum allowed by law.
But we're not done there! Oh no, we inspect every roof for completeness! This is something not every company will do, infact most will not inspect! I will inspect myself or send out another COMPETENT person to inspect the roof. I have preprinted inspection forms which look for more than 50 points on the roof. It happens occasionally that perhaps we forgot some caulking or something, but I check for clean up bushes, grass, window sills, neighbor's yard, gutters. I check for straight eaves, proper overhang at the eaves, straight rakes, proper over hang at the rakes, starters at the eaves and rakes, straight valleys, proper overlap in the valleys,
valley is installed in the proper direction so to shed water (lots of valleys get installed backwards), straight hip and ridge, proper exposure on hip and ridge,
ridge faces away from prevailing wind to shed wind (lots of ridges get installed backwards), straight shingle rows, proper nail placement, proper nailing pattern, proper nailing depth, flashing details, etc. etc. etc... Like I said it's more than 50 points and this inspection takes about 20-30 minutes on the average roof. Time is money! I once worked for a large company, I was the scheduling manager, they had 10 sub crews working on average each day. The owner once said to me very proudly, "If the customer complains we fix it!" But it didn't make sense to me, and still doesn't. The customer, the one who knows nothing about roofing, is the QC? They might not notice a problem with the roof unless the shingles are upside down (no offense to any home owners

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So you see I believe in my heart and soul that we are worth more, we are certainly doing alot more for the dollar. And having said all that we are also not the most expensive in the area, just to give you an idea of what kind of spread you can see from companies around here.
SO why did I spend my time writing all that? Well partially to inflate my ego, but also to show that not all roofs are created equal. There are alot of areas where people can cut corners. Let me say that again, ALOT of areas where people can cut corners. Look at the price of the roof LAST, look at the "Recipe", what you are actually getting first. Again, quality of materials and scope of work will dictate price.
Now as for Gary not caring what people think about him, I can appreciate that. But he better damned care what his customers think about him or he's losing alot of jobs. If he worked for me, we definitely wouldn't get along with his approach.