I support the 3-month timing.
Having ridden from Virginia to Panama City, plus two long runs in South America, my observation is that the run down to Panama is not a great ride, as it's filled with ugly border crossings (seven) and less-than-spectacular scenery (although there are many nice and historic places, which tend to be the old cities). Recommend central route, as the coast highways are less scenic and busy with trucks. Overall, hassle per mile makes it not as attractive as South America.
And, don't forget to consider the Central America rainy season.
Bolivia is great (rode there twice), so don't miss South America.
If you've not done a trip like this, I'd recommend reading "Odyssey to Ushuaia" by Andres Carlstein (Chicago Review Press). Good reading and gives a useful view of the ride, plus thoughts to consider if you fancy riding with a friend or acquaintence.
Another very useful book is "Riding the World" by Gregory Frazer (Bowtie Press). Great for bike travel prep.
Good luck.
Yellowknife
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