Your timing looks good. When we drove from Colombia (left in June) we arrived in Ushuaia in November and this worked well for us. Note that we live in Colombia so the first part was just getting to Ecuador; we also know much of Argentina, and have since returned several times for a variety of reasons, and have "filled in some blanks" in the sense of spending time in bits of Patagonia which we either didn't visit on the "big trip" or where we wanted to spend more time. Let us know with specific questions and we can offer thoughts.
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