Enjoy the Adventure
Since you are building from the existing box in, there are lots of similarities between your project and the Stealth Camper I built. Bob86ZZ4 gave you the link to the thread (Thanks Bob). I posted a ton of pictures in the photo gallery. Just look for keyword "Stealth".
I tested R-max foam for crushing and found I could not crush it with 5/8" plywood on top. I did use supports under the seams, but nowhere else. In my case I used 1/2" foam under the floor, 1 1/2" in the walls, and up to 5" to 6" in the ceiling, depending on the arch.
Personally I figure windows are a liability, but many can't imagine living without them.
I have to tell you, just this once. You can probably buy something close to what you want far cheaper than building it. (but building is more fun...) Others will tell you the same. I spent over $40K on my little 14' box truck. The good news is that you will get exactly what you want.
Oil based primer and latex top coat? Sounds like a bad idea to me. I was told you can put oil base over latex, but not the other way around. The latex will not adhere properly and will blister. Assuming you are talking about the outside, I am not sure that any type of house paint is the way to go. Then again, I am no paint expert.
Good luck!
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