Replacing Shingles/Flashing

Hi,
I have a somewhat difficult situation. I have a roof leak around my fireplace chimney (pretty certain of this) and I am considering replacing the flashing. There are a couple of problems with doing this. There are 4(!) layers of shingles on the roof, and the roof sheathing does not appear to abut the sides of the chimney surround (at least looking at it from the outside - the drip caps do not extend all the way to the sides of the chimney surround either).
The top layer of shingles was installed just before we moved in and the roofers apparently put in new flashing just underneath the layer they added. IOW, the flashing is not attached directly to the sheathing.
Is it too big a project to remove all the layers of shingles around the chimney, replace any sheathing and flashing as needed, then reshingle for the average do-it-yourselfer? I have or can get everything I need to do the job and I'm pretty good at doing stuff if I have enough information.
I know the best thing to do is strip the entire roof of shingles and start anew, but the expense of doing so is prohibitive, and the roofing industry is rife with shysters. OTOH, this may be too difficult and time-consuming for me.
Any opinions on what I should do, short of burning the house down, would be VERY much appreciated. The top shingles are only about 10 years old and I have no leak problems anywhere else.
TIA, James
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It may be as simple as re-sealing the existing flashing. Buy a couple tubes of roofing cement and re-seal the top of the flashing around the chimney and any other gaps or cracks you can see.
John

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in article snipped-for-privacy@powergate.ca, John at Don't_Spam snipped-for-privacy@msn.com wrote on 1/25/04 7:21 PM:

I forgot to mention that I had done some resealing, to no avail. I'll look again to see if there's anything I missed, but I doubt it.
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in article BC39C06F.63A8% snipped-for-privacy@hotmail.com, James Harvey at snipped-for-privacy@hotmail.com wrote on 1/25/04 7:50 PM:

i am no expert, but i know you have way too many layers of shingles up there. what state are you in, and check and see if they allow that, i doubt it. strip it down and have it done right.
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in article BC39D69F.8EDC% snipped-for-privacy@columbus.rr.com, charlie at snipped-for-privacy@columbus.rr.com wrote on 1/25/04 7:24 PM:

As I said, that solution is cost-prohibitive at this time. And yes, the roofing is up to code (Texas), liberal as it may be. I am looking for a short-term, inexpensive solution, whether I do it or not. My main question is on the advisability of doing it myself. Thanks.
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4 layers of shingles ?!? Sounds like the water is riding down the flashing, under the 'good' shingle layer, and leaking through the rotten old shingles. Or they didn't properly bed the upper flashing in the slits in the mortar, and it is leaking down the chimney surface. No good way to tell w/o seeing it in person.
Do you plan to keep the house? If so, I'd bite the bullet and get it ALL ripped off and redone correctly, even if you have to take out a refinance note to do so. The bank will understand- it helps keep their security on the first note in good shape. Letting the roof go bad is probably THE quickest way to kill a house, short of fire. On a multi-layer roof, 10 years is over half the lifespan you can expect. You can cut the cost by doing the stripping yourself, if you can coordinate schedules with the roofing company and have friends you can draft, and a big truck to drop the mess in(and it WILL be a mess on the bottom layers) as you scrape it off. Ask friends and coworkers who did their roofs, and go the library and look in old city directories to see who has been around a few years. Shysters and con men don't last long. Get bids from several long-term companies, and ask for addresses of jobs they did several years ago so you can drive by and see how they are holding up. A quality company will have no problem with that. A quality job, with quality shingles, won't be cheap. But you'll Never Have To Worry About It Again, and that is priceless.
aem sends....
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Thanks. That's the best advice I've seen so far. We're planning to sell the house so we just want to get the leak itself fixed ,so a buyer can't claim there was an undisclosed problem with the house. :(.
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James Harvey wrote:

if you have a access to the attic, please check the sheathing of your roof. it may be that the weight has bent the edge down around the chimney. also you may have alot of rotten wood up there from having four layers and the decking or sheathing has not been checked for a long time. if the buyer gets a inspector you may have trouble selling the house.
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James wrote:>Is it too big a project to remove all the layers of shingles around the

>TIA,

roofed for 20+ years in Michigan. It's nice to have sheathing right up to the chimney as a nailing surface, so I'd suggest tearing off around the chimney. You could go a couple ways from here. Cut away the underlying shingles and apply plywood to bring the substrate up to the level of the 3rd layer, then re-roof, or replace the original decking, install cheap shingles up 3 layers, then roof and flash the final layer. Flashing instructions are on every bundle. Tom Someday, it'll all be over....
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