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I have a 17' Montauk. Love it! This winter I'm hoping to give her the TLC she needs and deserves. unfortunately the previous owner painted all the woodwork, which I plan on replacing. What I need advice on is this...
A friend of a friend does fiberglass work. He said he would wrap the entire hull (inside and out) in a layer of fiberglass, replace a spongy spot in the deck and gel coat her for around $1600.00. The glass isn't all that bad, just not very good looking. What I want to be sure of is that she gets dried out, and keeps water out so she's around for the rest of my days. Is there a better way to go about it? The price sounds good for the work he'll be doing, but I don't want to ruin her either.

Thanks,
Chris

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First thing first.
When you have her out of the water and on dry dock carefully inspect every inch of her structures, map out the extent of the repairs and make a decision on the actions to be taken.
In my opinion, a refit is not something that should be done half fasted.You may want to verify that the recoating will be gelcoat or paint.The fee sounds reasonable enough.
I have spent more than that in supplies and parts for my personal work here.

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Yes, he did say gel coat. I agree, I don't want jump in and have a patch job that's going to hurt her more, as she isn't that bad now. Is adding a layer of glass a legit method of restoration? I pretty sure the hull to be sound and solid, my big concern is keeping her dry.

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Check some if work out.
If you like his art, give him your contract.
If I was you i'd consider the sanding method first.
Carefully sand a section of your surface with 400 to 800 grit.Wet or dry and see if your gel coat can be brought back to newness by simply doing this.
I would seriously consider this option before jumping the gun and resurfacing.;)

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Thanks Serge, I sure will! Keep you updated, hopefully I'll be on the water in a like new classic Whaler next summer.