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Sounds like a great adventure.
I did a trip from September until June, through France Spain and Portugal. I loved it. Head south for the cold months, and you’ll be fine without any sort of heater. January and February can be wet and the days are short, so just be prepared for that. Portugal, Spain, Italy and Greece are popular winter stops.
An pop-up awning is not great if you are wild camping, as you need to not actually be camping, but effectively just parked. It’s OK for campsites. It will probably be fine for some areas, but not all.
Most people dont collect too much as they go. If it all fits in well now, you should be fine. however, a bit of extra space is a good idea, although not essential.
Have a great trip!