Roof Leak around chimney

My chimney definitely needs some new flashing around it. I have a leak and water has gotten into the attic area and started to cause the plywood below the chimney to warp and bend. The roof has two layers of shingles on the roof. The 2nd layer is less than 10 years old.
At this time, I would like to stop the leakage with getting the flashing replaced. I am thinking that the warped plywood can be replaced when we reshingle again in 10 years or so.
Our chimney "top" above the roofline has a "brick look" asbestos material. It seems to be in good shape.
I have gotten a couple of suggestions and not sure which is "most sound". Naturally, my goal is to get the remaining 10 years left out of the existing roof. Which sounds like the best solution?
1) Tar/seal around the chimney. (Cheap $100 - but will it work and for how long?) 2) Replace asbestos chimney top with aluminum/stainless chimney through roof and replace entire section of roof. Roof replacement = $1300 (doesn't include new chimney cost). 3) Reflash around existing chimney (Inexpensive $250 - should work - new leaks to be concerned about? I asked the roofer about removing existing shingles and he said he should be able to tuck the flashing under the existing shingles (keep in mind there are two layers!). I have a feeling this isn't going to work well - but he didn't think the chimney top brick stuff was asbestos.
I know option #2 is probably the BEST solution to ultimately fix the situation, but I dont really want to put up a new roof when the existing roof still has half its life left.
Any ideas, suggestions? Dom
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I'd go with the re-flashing, if the roofer is OK with it- probably wasn't done when the second layer was put down- probable source of your problem. Have him check other flashing/ penetrations while he's at it.
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Sev wrote:

No - it wasn't....
Dom
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The other thing to note too, the roofer that suggested the flashing replacement only did not go up on the roof. However, he did go in the attic and agreed the problem is coming from the chimney flashing. I guess I am concerned that if I go with him for the job, he will get up there and discover it cant done because the chimney is in fact asbestos "brick look" and he can't seal the flashing properly to it. Is that a reasonable worry?
Thanks - Dom
snipped-for-privacy@gmail.com wrote:

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No.
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Edwin Pawlowski wrote:

Just learned that the "fake brick asbestos" around the chimney is referred to as the chimney surround. Any idea how much a new one of those cost (installed)? I hate the thought of the metal chimney showing coming thru the front part of my roof.
Dom
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snipped-for-privacy@gmail.com wrote:

You can also try to seal up the gaps with some Great Stuff. http://greatstuff.dow.com - worked great for me when i found out mice were coming into the attic from the gab between the chimney and the roof!
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what condition our the existing shingles? we know they are 10 years old. are they losing granules? corners wearing? or l;ooking spiffy?
in some areas like phoenix shingles age faster than others.
if you are planning on selling anytime soon or if the shingles are aging you may be better served by a whole new roof.
apparently whoever added the 2nd layer of shingles didnt replace the chimney flashing, that probably means the vent flashing, drip edge etc are all at the end of their life too.
thats why i say consider a new roof, once done its a asset to your home
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