Things to consider - money, what you want to see, what kind of riding you want to do(hauling you bike through mud bogs/sand traps, riding the Interstate), etc. Different for us all, make the best guess you can, don't be surprised if you choices change.

its Colombia
 

I worked here in 2016 - 2018 It is my home and residence
I had Big plans for touring SA when I arrived the first week in march last year after a 5 month deployment with my work, Well covid put the brakes on that
Hell a year hasn't cost much especially from March to September last year
Colombian authorities were very strict and you could not travel anywhere
Me thinks this year is a right off I would not make plans to cross border travel this year. Many people got stuck last year I got stuck in my paradise
and do a lot of riding in this beautiful country, Over 50000 km in Colombia since 2017

Interestingly we've found that on our "big trips" the average daily Km are almost identical .

2010-2011 161 Km/day - South America
2017 168 Km/day - Africa
2019 169 Km/day - Australia

Speed
 

I have read stories from several long distance travellers.
And they often end up in the same range as mentioned above.

Around 1 000 km/week as average over a long time period.

Of coures with differences depending on all the factors already mentioned.
=
Medellin-Ushuaia shortest route is around 10 000km.
Add 50% for the actual route => 15 000 km
Divide by 1000 km/week => 15 weeks

Lets say 4 months.

It depends too on the self sufficency and off grid capabilities.

If I find my personal remote paradise with "no time pressure" - and fully restocked with a full fridge, full freezer, enough food and beer - I wouldnt leave before the weather will kick me out - or I run out of food/beer.

That is around 12 days - till we need to leave for restocking. Solar power we have enough during summer time.

Guess without any timeframe and money restrictions - I would use such breaks more often. Enjoing the nature. Wildcamping, Campfire, bbq, reading books, hiking.

But that is too because the rig even has his comfort, with hot shower after the hike, has a fridge, has a freezer - enough solar power to keep everything running - extended.

http://2.bp.blogspot.com/-eqgMF06Z7e...600/Dusche.jpg


Surfy

As noted in a previous post, we took 4-1/2 months.

I took a couple of months heading south, and about six headed north. Both directions felt kind've excessively hurried.

Just a thought to add to your options.

I rode down and arrived in Ushiaia on the 1st of November.
Some of the places to stay in Chile were a little Spartan as the season hadn’t really started yet but we had mostly great weather and empty roads.
It was completely stunning down through Chilean Patagonia and we never once had to wait for ferries, hostels, or anything else so I’d like to recommend arriving early. Everything was also of course cheaper too.

Have a great trip.