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With a HD and a trailer of that weight there’s no need to over think things. Just pick the trailer you want and the one that works best. Hooker up and let her eat.
If it is warm while your heater is on then it is possible the carpet is laid overtop of the rear seat heat ducting. On my 19 I had to remove the tray and straighten out the carpet as it was blocking almost all of the air flow to the center back seat outlets.