seeing how your going over plywood, i would prep the plywood first.
if you want your trailer to be 100% watertight for 30+ yrs, and twice as strong as just plywood alone, i would coat the entire trailer in PMMA.
we use Soprema Alsans RS 230 flash at work, it's a 2 stage coating that is impervious to water, gas, chemicals, and damage. you can beat on this stuff all day with a hammer and not even scratch it. you can even drive a vehicle over it with no damage at all.
you mix it up just like body filler and can brush or roll it on. it is self leveling, so if you want texture, use a texture roller. comes in grey and white, but can be painted any color you like. this stuff will not flake, peel or anything, gives a rock hard coating that is still flexible
i did my camper roof with it few yrs ago- i now have a literal "forever roof" with no maintenance what so ever. and it's lightweight, 2 coats added approx 6-8 lbs to my camper roof
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it rained about 20 mins after i did my roof, check out how the water just beads
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this is not the "snow roof" junk you get at the rv or hardware store, it's an extremely high performance coating that you can only get from a dedicated roofing supplier. this stuff will bond to anything, plastic, wood, metal (any kind) rubber, just about anything you can think of.
and because it's so good, it's not cheap. this 25lb pail runs about $200 plus a couple more bucks for the catalyst, but for never having to do anything with it again is more than worth it.
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like i said, it is impervious to water, my car topper boat was leaking around the engine transom board, coated it with Alsans and added some green paint to match, and no more leaks at all
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one thing you should do if you use it, is use the fleece over the gaps around the edges, kinda like a filler for big cracks or joints
a version of PMMA is actually used to make fighter jet canopy's.
here's some info on PMMA
and
Two-component polymethyl methacrylate-based (PMMA) liquid membrane combined with fleece fabric to form a monolithic, self flashing and self-adhering reinforced field membrane designed for use in interior and exterior new, tear-off and recovery application
www.soprema.ca
it is an easy to use, do at home type of product, just
MAKE SURE you use rubber gloves, only time (and lots of it) will get it off your hands. no paint is going to last many yrs, but you will have a super solid substrate to keep working with for future paint jobs.
one of the better paints i have ever used is POR15, incredibly tough paint, the entire underside of my truck is done with it