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WEICK BUILDERS
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When to Replace your Roof

Tear off or shingle over

Roofing ventilation

This one is relatively simple, BEFORE IT STARTS LEAKING!  But for real, this is complicated. If you have a leak you may only need a repair. If the leak is not caused by wind or tree or hail damage it is probably a good sign that your roof has reached the end of its life, or that it was installed incorrectly.  If the roof is aged, beyond a repairable state such as the shingle are too brittle to me moved to interlace new shingles your local roofing expert will recommend a new roof otherwise you may end up causing more damage than actually fixing the immediate problem.  We get called out frequently to quote a repair and in some cases it is just that, replacing a few wind blown shingles or a tree fell on a roof and damaged shingles or more. but just as frequently if not more we find a roof has aged beyond repair or the last roof was not installed properly and to take on the repair would create to large of a liability to make it worth us doing the repair.  some examples are there are too many layers of shingles on the roof exceeding the Building Code for our area which is 2.  Or the previous roofer didnt install a roof vent properly or the chimney flashing properly because there are multiple layers of roofing.  So get a licensed and insured and manufacturer certified roofer like us to come and look at the roof. Most of us do it for FREE!  
We receive many calls from potential clients asking if we could come out and quote them on a shingle over.  I will set the appointment and go out and begin by introducing myself, learning a little about what the owner is trying to accomplish, then I will do a roof inspection and get some measurements if I dont already have a satalite.  I then begin the process of educating the customer on what a proper roof job looks like and what the local code requires.  In our area, the building code will allow for up to 2 layers of shingles on a roof.  We will never install over the top and here are the reasons why
1-We cant see what is under the shingles, if the last roofer did do a roof over it is usually quite apparent, but it doesn't mean we can tell exactly how many layers, I also see occasionally that the previous roofer has tried to cover the fact that there are too many layers by using fascia to cover all the old layers and then put a 1 layer T-style drip edge on.  
2-we can;t tell if we are going to be nailing to damaged or rotten wood so we can't be sure the nails are going to hold the shingles down. we can frequently do an attic inspection but sometimes this is impossible or even if you can see the bottom of the boards you may not be able to see any rot or damage on the top
3-we cant properly flash walls or chimneys when shingling over. we could try to tar and seal those areas but that doesn;t last and doesnt look good.
4-the shingles are not going to last.  the more layers of shingles, the more heat absorbed from the sun and from heat escaping from the home. this literally bakes the shingles cutting the life expectancy of the shingle by 1/3 to 1/2 or more.
5-we can't be sure the roof meets code.  Underlayment and ice and water requirements have changed and applying another layer of underlayment or ice and water won't allow either of those products to do their job completely. 
6-Warranty -  every shingle manufacturer is different, but all of them will reduce if not eliminate the factory warranty if a shingle over is done.  secondly, we are required in our state as in most states to offer a workmanshinp warranty and if we cant to the job right then we dont want to do it at all and get stuck worrying everytime a phone rings that we have to go try to fix somethingthat was never noe right in the first place. If a roofer says they can save you money by going over your old shingles, they are lying to you. it may save you a couple dollars now, but over the life of your home it will most assurdly cost you twice as much.
Yes, your roof and attic need to breath, underventilation of the roof will cause premature roof failure.  what type of vent to use is a debate that will last for years to come.  In our climate I personally prefer to use ridgevent whenever possible, but we have a lot of older homes with cut up attic spaces, upstairs bedrooms with knee walls and such and in many cases a box vent or a turbine is more appropriate to ventilate the entire roof.  make sure your roofer calculates based on the manufactures specifications what air flow your roof will require and design enough ventilation into your roof to make sure your roof lasts.  dont just replace the 1 or 3 pot vents the last roofer or builder put on, that likely is not enough
You won't hear advice about doing your nails or applying makeup, we may tell you how to use nails and how to make over the exterior of your home though. We hope you enjoy!