I have read a lot of info on this forum (especially from Andy at Inland RV) about the need to replace the window gaskets on vintage trailers, as they are a prime source of leaks. When mine started leaking, I bought the gasket material and 3M Superweatherstrip and tackled the task. Cost was about $70 for the five windows on the Caravel. (For a few bucks more I should have done the door, too!)
Thought I'd post a few pics of the process for those who want to do this themselves. It's not hard, and from what I've seen, most 60's trailers have window gaskets as bad or worse than mine, so it's a widely-needed fix.
First picture shows the window gasket as you'll see it on many trailers. This was a double-flared gasket once, but it has been compressed and dried out for so many years it is like a single piece of hard rubber. Amazing it still worked as well as it did!
With a metal putty knife you can easily slice off the bulk of the old gasket. Just run it around the edge. You'll leave a black stripe of leftover material, which is removed in the next steps.
3M makes an adhesive remover that works great. We tried acetone and some other solvents, but the 3M product was definitely best. It comes in a red can.
With a brush, you just spread it over the remainder of the gasket and wait a few minutes. Don't rush it -- let the remover soak in before you try to scrape again.
After the adhesive remover and first scraping, you should have something like the picture below. Brush on another coat or two and wait another few minutes before proceeding.
If you scrape without letting the adhesive remover do its job, you'll just work harder and be left with a hard yellow-ish remainder of the original adhesive. If you let the adhesive remover soak in with multiple coats, you'll find that both the gasket and adhesive come off together nicely.
Finally! After two or three soakings and scrapings, you should have a very clean bare metal surface like the picture below. There's no need to sand. This is what you want, so your new gasket will stick perfectly and not leak.
During this process, I found blobs of silicone caulk in various places. This was not hard to remove, just annoying. But in the bottom left and right corners of this picture, you can see some black blobs. Those are old Vulkem caulk. Not sure if they were factory or prior owner, but they didn't want to come off and ultimately I left them there since they didn't interfere with the new gasket.
The next step is to put on the new gasket. Andy from Inland provided straightforward directions in this thread . Basically you cut the gasket to length, put the adhesive on, and stick it in place. Not hard at all.
Note that he was replying to someone with a 1970 window. For the late 1960s windows (at least mine), the gasket only goes on three sides. As a result, it's not necessary to remove the window in a late 60's model -- you only have to open it fully.
I followed the directions on the 3M Super Weatherstrip adhesive, which says to put a thin coat of adhesive on both the gasket and the window frame, let both dry, then put another coat on the gasket and apply it. If you do this, it can be adjusted as needed for a few minutes.
Be careful not to stretch the gasket as you apply it, especially in the corners. Cut it a bit too long before you apply the adhesive and then trim to length after you've installed all but the last inch. I found that leaving the window open for half an hour allowed the adhesive to set where I wanted it, whereas if I closed the window the gasket tended to move.
I don't have pictures of the new gasket going in (because I needed three hands to do it), but it's easy enough if you have a helper. Any adhesive that gets on you or the trailer comes off easily with the 3M adhesive remover.
Heidi, I got the gasket and 3M Super Weatherstrip from Inland RV. They know the size of the windows and can sell you the correct length of gasket if you tell them which trailer you have.
My father already had a can of the 3M Adhesive Remover but I expect you can find that locally in hardware stores. Contrary to what I said above, it's a white can with red label.
Inland did recommend two tubes of 3M Super Weatherstrip and it turned out that I used only 3/4 of one tube to do all my windows. So if you want my spare tube I'll send it to you (since you're a fellow Caravel owner!)
I read through the thread about the gaskets and now wonder if you need to replace the mechanical parts of the window?
The cranks on the '68 Tradewind (Chad's) work fine, but the latches that telescopes out have broken on a few of the windows. Any suggestions on where to find replacements? We could have them fabricated if need be.
Rluhr-
Sure I'll take it. (I'll pay you for it too.) I should order the weather stripping soon. There are only a few months out of the year that one can do anything outside in New Orleans!
The adhesive is applied to both the gasket and the metal window frame. When dry to the touch (about 5 to 10 minutes) you then carefully place the gasket in position.
With this process, we in our shop use one tube of adhesive per 20 to 25 feet of that type window gasket.
If both surfaces are not coated with adhesive, a long life bond will not take place.
As a general rule when using adhesives, too much never hurts, but an inadequate amount will not bond the gasket to the metal correctly.
FWIW: I've been working on doing mine....I followed the directions on the 3m adhesive label, and wound up using WAY more than Andy describes. I used 3/4 of a tube just on the front window alone. its a big window, but still.... I think I'll try Andy's method on the next one I do. It seems like the thin layer on the rubber weatherstripping actually gets absorbed by the rubber. maybe that's just because it is the same color as the glue (?)
Also: I got some 3M adhesive remover, too. (both the super-gasket adhesive and the remover were stocked at my local wally-world). It didn't come in a red can, though...wonder if its the same stuff? It says on the label that its a combo of xylene and naptha..some other stuff too. didn't think it was any better than straight xylene. It was a biotch to get the old stuff off of the window frame. maybe I didn't let it sit long enough. Anyway, whatever they used on the main entrance door gasket was really tough....it was very hard and brittle, and the xylene wouldn't even touch it. had to use a wire brush and dremel tool to "grind" it off.
Chuck, sounds like you might have just had a tougher adhesive. But I did find that leaving a bit of the old gasket on before applying the remover helped keep the solvent in contact while it worked. If I scraped off too much of the old gasket first, the solvent would just run off and the window would take twice as long to clean up.
The first window took me 45 minutes, but by the last one I was knocking them off in just 20 minutes.
I didn't experience any absorption of the adhesive by the gasket material. When I applied it, it stayed in a firm linear bead along the length of the gasket.
BTW, I applied at nearly the rate that Andy's shop does. The five windows in the Caravel (3 sides each) equal about 23 linear feet of gasket. I used a bit more than 3/4 of a tube to do that. I could have used a full tube if I were a bit more generous, but no way was I going to use two full tubes -- that would be 11.5 feet per tube. The gaskets are quite secure and tested watertight.
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I think I'll try Andy's method on the next one I do. It seems like the thin layer on the rubber weatherstripping actually gets absorbed by the rubber. maybe that's just because it is the same color as the glue (?) 
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