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Zacs-
My father has the same boat as you, year and all,and he is looking at the same repair job. I have looked it over for him and figure it would take 2-3 weekends and about a grand with some decent sweat equity.
I have done a couple of transoms, one on a 20 seacraft and the other on an older Grady.
Knowing the lay out of your 19 I can all but gurantee you can do the transom / Deck job your self for around a grand, even less if you buy the cloth over ebay.
The job is alot more daunting than it really is. if you have any hands on skills and can cut a somewhat straight line you can do it yourself.
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