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answered any of your questions, I'll give you my thoughts based on owning an Arctic for 7.5 years. I expect that one of our experienced N20 owners will eventually post and I would trust their opinion over mine.
First and foremost, my Arctic is an extremely well built boat and from all accounts the N20 shares the same quality. I know that for a 15 year old boat, mine has held up extremely well.
From reading your assessment of the boat, my biggest area of concern is the rudder and rudder mount. Obviously, somebody has done some work there and this is probably not good news. You may want to discuss this with Paul Miller who frequents this board. I know that he had rudder mount issues with his N20. I bet that you can find some of his posts on the subject by searching the archives for this board. As for the rudder itself, major gel coat cracking is frequently a telltale of underlying structural issues. I would certainly fully address both the rudder and mount issues before using the boat. Being up a creek without a rudder would not be fun and could be dangerous.
My next area of concern is the lifeline leak. This could be nothing more complicated than taking it apart, rebedding it and tightening some bolts. It could be much more work if there is delamination and/or damage to the core material.
By window gaskets, I assume that you are referring to the rubber gaskets which make seal between the port hole frame and the opening window. If so, you should be able to find replacements on line. I know that WM carries the ones for my Arctic. If you are referring to the seal between the porthole frame and the fiberglass, this will be a bit more work. You will have to remove the ports and rebed them. Make sure that you look for damage to the core material.
Running and standing rigging are easy. Take your standing rigging to a rigger and have him make new per sample. Don't scrimp on this because a shroud breaking under load may mean a new mast. I do not know what this will cost but I will be able to give you an idea in a couple weeks since I am replacing mine this week (hopefully). You could also have the rigger make new running rigging but you can save money by doing this yourself. You can buy a fid kit for ~$40 and do the spices yourself. It is not hard and makes a good winter project in front of the TV.
The hull is another easy one. The bottom will clean up nicely with a pressure washer. You will not need to repaint the bottom unless you plan to leave the boat in the water. If you do this work yourself, make sure that you follow appropriate environmental laws. The fading of the hull above the waterline is a common problem with Nimble green. I have used both Ploiglow and Vertglass and both do well. Vertglass has a better look but is much harder to apply. I now use Poliglow because it is so much easier. I'll bet that about 8 hours with a Poliglow kit will make the hull look real nice (see the pict below).
The sails are something that you can defer unless they are torn. Having old/baggy sails is not a big deal unless you race and I doubt that you will be racing a N20.
You'll have to further explain the problem with the hull liner. I am not familiar with what you are talking about.
I hope that this helps. Mark
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