Sue and I have had our 5x8 Diamond in the Rough for a little over 2 years now. In the summer we manage to get away to Awenda Park a couple of times in the summer and take a longer trip in the fall, when the kids are back in school and everything is less crowded. Last year we spent over 3 weeks traveling around the east coast and are heading back again . It got pretty chilly near the end of September but we stayed warm and dry, although we had to use a small space heater a couple of times. We found the walls pretty cold at times like that so I've put closed cell foam from an old sleeping pad along the headboard end with double sided tape and a carpet runner along the wooden walls between them and the mattress and about 6 inches above. It makes quite a difference.
We use an 8x10 pop up shelter over the back half of the trailer in the rain so we can use the galley without it getting wet. I have a portable solar panel to charge the battery and a waterproof Noco plug installed on the front of the box to plug in external power with the lid closed. I also have a Noco Genius on board charger and a 1500 watt inverter. Once after driving in heavy rain I found water inside the box so I tightened the lid down by adjusting the latches and that seems to have solved that problem. I recommend you buy one of the
trays for the front box from Lowes. They're a bit pricey but worth it.
One tip I'd like to share with you is to put your ice inside a dry bag in the cooler. We use a Woods 10 litre size. You still get some moisture from condensation but the melting ice is kept contained in the bag. It keeps your food from getting waterlogged.