Hi Geff,
I myself am doing what your planning. I'm in Ecuador now. I went BA, to Ushuaia and then followed the West Coast up.
One thing you may want to keep in mind is the passage from Colombia to Panama. People say the boat trip is a fantastic experience if you get good weather and a good boat. I would recommend the Stalleratte if you can manage to organise it with their schedule. Supposed to be lots of other bikers and a great trip. Unfortunately they are not available so I am using the Independence.
But as you say you want to be north earlier to miss the rainy season, you may end up hitting the stormy season for the boat trip (jan and feb) and have a rough sail, or some boats refuse to go during that time.
Of course if you take a plane this is no problem!
Ps. I was in Ushuaia for Christmas and new year. I think every year there is a bikers party at this time at one of the campsites. Was great fun and met some great characters...could be worth holding back for!
All the best and good luck!
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