Welcome trucker Joe.
My Hi-Lo had a big roof A/C that contributed to all of it's water damage when the roof buckled a bit and cable tear outs from the rot and heavy top. I agree the normal window A/C mounted in a cabinet in the wall is better. Many of the new inexpensive models of travel trailer have these. For my size a 5k btu is plenty, they cost much less, don't add to drag, and can be powered by a single small quite generator (like you said) if need be. The money you save compared to buying a roof one about pays for 1/2 the generator.
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