Ice and water shiled - should I install it?

Hi,
I have two small water stains on the outside wall - one is by the chimney, another one is in the corner or the house. The stains appeared back in December when temperature dropped sharply.
It looks like that there is not enough roof ventialation because the roofing nails are wet and rusty.
A contractor suggests to install the ice and water shield on the portion of the roof where the stains are, including around the chimney. He needs to remove three feet of shingles, install the ice and water shield and install new shingles. He quoted me $1500 for the job.
My question is - will it solve the problem? Shouldn't I just fix the chimney flashing and improve ventillation?
The contractor is saying that builders newer install ice and water shield in newer houses. I've heard it many times from many people, but isn't it optional?
The roof is nine-years old and in a good condition...
Thanks,
-Stan
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$1500 sounds like a lot of money. I had a quote for an entire roof, including ice dam all around the house and a new skylight for around 5k. Look into this with other quotes.

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That's what I thought too... The materilas are probably $200-300. Nobody in our neighboughood have these ice and water shields. The way I understand it is nice to have, but it may not solve the problem (water stains)

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Stan wrote:

Get a second or third opinion. It is difficult to see from here exactly what that roofer saw, maybe a problem with your roof or maybe a boat payment.
--
Joseph E. Meehan

26 + 6 = 1 It's Irish Math
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Stan wrote:

Get a second or third opinion. It is difficult to see from here exactly what that roofer saw, maybe a problem with your roof or maybe a boat payment.
--
Joseph E. Meehan

26 + 6 = 1 It's Irish Math
  Click to see the full signature.
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I'd really worry about "the roofing nails are wet and rusty". Where is tha moisture coming from? The house below? Temperature changes? Maybe the roof space/attic is not correctly ventilated. Mould and rot possible?
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