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Amazon product ASIN B01GL78U8O
Here's the dehumidifier. Your question about being too dry? Not that I noticed. Typically I wake up covered in moisture from the air when I camp and its hot in the tent or camper. With that little guy in my 50 sq ft it was great.
And you can set the humidity level you're happy with - so if it's too dry just bump it up with the little digital thingy... Only drawback, it's water capacity is tiny. But it has a hose attachment too.
The AC:
Amazon product ASIN B01DLPUWL2
It's about 250 now - the reviews aren't great, but it's the smallest btu I could find for a reasonable price.
The dehumidifier is nice and compace versus a shorter, wider one which is nice for tucking in a corner. If I were you, I'd get both of these and build a little corner for them to fit into and strap down.
For the AC output hole, I used one of these: (not this one specifically - if you end up going this route, I'll search some more and find you the exact one I used.
Seasense Waterproof Deck Plate
Open it when you use the AC, close it when you don't. nice and water tight.
Crap, no clue why those amazon links went bye bye... lmk if you need me to get you them.
If you could link me to something at least similar to what you have, that would be awesome

I'd really reconsider osh. It wont like the vibration of road travel, as well as all the extra glue involved in making it will offgas for a while.
Ply or marine ply is your friend. Do it right once, so you dont have to do it over later
I have put significant time and expense into doing it right, but I appreciate your willingness to help. What evidence do you have that OSB won't like the vibration of road travel?
The OSB is sealed on both sides with epoxy/fiberglass, so offgassing is not a concern. People have built boats out of OSB, I doubt this will see more abuse than in a boat.