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Thank you all for your input and that your experience is helping me to determine my best course of action. To answer the question the paint is mainly chipping on the hall the boat. I think because they were stored in a shed, that boat was on top of the other and stacked at the top of the shed. Over the 47 years of no use while in the shed, the heat in summer months that rose to the top of the shed weekend the paint overtime causing it to become brittle. The paint started to chip off after I transferred the boats from where I found them to my house which was approximately 20 miles. The twisting of the boats while strapped to the trailer in transport caused the brittle paint to crack even more and start to chip off. I am going to be working on them today taking the seats out to repair the cane. The one boat that has the chipping paint I plan to continue shipping away the existing paint if possible to further exposing the condition of the canvas and filler which I believe to be intact. I then am asking you all should I water test it for leaks? If the boat leaks I have no option other than replacing the canvas at that point. If it doesn't leak should I repaint as described in the process posted by mccloud?. Does that sound like a feasible plan? Look forward to your response respectfully Greg
 
Water test it for leaks. If water doesn't gush in, dry it out , sand and paint with cheap enamel. The chipping paint is typical of Old Town canoes made without white lead based filler starting in the 1960's or so. The filler will completely chalk away in spots. The condition will continue, that's why the cheap enamel. New paint chipping can be touched up as needed. Use the canoe as long as possible before installing a new canvas.
 
No paint job is any better than its foundation – a good sub-surface is critical. Painting over peeling paint is pointless – the old paint will continue peeling, taking the new paint with it. New paint will not keep old paint from flaking, but will simply come off as the old paint keeps failing.

Is the old paint at the edges of the chipped-away areas really tight, or can the chipped areas be easily enlarged by lifting up the edges of the chipped areas? If you can chip paint away, can you get to an area where you can’t chip the paint? If the later, you might be able to prepare the hull and apply paint that will be serviceable for a few years. But given that the chipping away of the old paint is scattered over most of the hull, and given that the crackling of the paint is very extensive, I expect that the old paint will continue to chip away and fall off.

Below are links to some discussion about this issue, and how you might proceed if you judge that the existing paint is sound enough. As you will see in these discussions, I have re-painted an old canoe and successfully gotten a few years of use from it. But your photos show much more missing paint than I had to deal with, and your paint seems to have come off in large pieces, indicating some sort of failure of the paint to adhere to the filler. A new coat of paint will not cure such a problem.

Your canoe well may not leak much even in its current condition -- if the filler is uncracked, it will keep water out even with the failed and failing paint. But something has caused that paint to come loose over a large area of the hull, and even if the hull is water tight, I would expect continued paint failure.

And as has been mentioned, if you do go ahead, do not use paint stripper to remove the old paint from the exterior .

http://forums.wcha.org/showthread.php?t=5790 see pp. 2-3 of this thread
http://forums.wcha.org/showthread.php?7769-Painting-over-existing-paint&p=41339#post41339
http://forums.wcha.org/showthread.p...t-Restoration-advice-please&p=32358#post32358
http://forums.wcha.org/showthread.php?7775-Temp-repair-to-bare-spot-on-canvas&p=41357#post41357
http://forums.wcha.org/showthread.php?7619-time-is-not-on-my-side!&p=40689#post40689
http://forums.wcha.org/showthread.php?8564-Smoothing-Canvas/page2 starting at post 12, on bondo spot putty
http://forums.wcha.org/showthread.php?6607-sanding-or-not&p=35286#post35286
http://forums.wcha.org/showthread.php?8906-Repaint-Tips

Greg, thanks for taking the time to post the links to these various threads. I will be having some questions about paint in the near future, and this is really helpful. thanks.
Jim
 
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