The overland truck companies used to do a complete circuit starting in Quito, heading all the way south on the west side to Ushuaia then heading up the east side to Brasil then over the top through Venezuela and Colombia and it took 28/9 weeks depending on the company. The trucks usually didn't go faster than 120km/h, but there were only a few places where they stopped more than 3 nights (usually a jungle excursion, time in Cusco for trekking, time in Chile (Torres del Paine and Chalten) for trekking, and a week in Rio over carnaval. Quite a rush, with a lot of kms. Your itinerary appears shorter, but you get a lot more feel for a place if you stay more than a couple of nights.
Gut feeling is 5 months minimum if you can manage it. Hopefully someone on here can give you a more direct answer, but I'd say go, travel at a comfortable pace, and if you run out of time, well you'll have to come back again!
Ride safe,
Simon.
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