I have pretty simple algorithm.

1. Is it in the general direction?
2. Can I get there in roughly 1-2hours?
3. Does the general scenery look nice en route?
4. Any points of interest to check out?

planner.flightsimulator.com/landing.html

That's a really good question! I was on "live" so it should be real-season.

Finding the same - I have turbulence set to medium, but I'm bounded around in what should be relatively still air. Going to be wild as I get closer to the equator at this rate.

Just an un-announced light aircraft without a registered flight plan and a stack of anonymous boxes flying over South America, nothing to see here, move along ;)

Headwinds, storms & mountains. Occasionally getting a bit lost trying my luck at dead reckoning. Learned a lot since then though - maybe time to ditch the floats.

I carry a jetski and a jerry can wherever I go, you know, just in case. 😀

Saved me redoing a bunch of legs last time, mostly running out of fuel in very isolated parts of Africa. Water landings don't count as a crash!

That's impressive! Subscribed on Youtube.

When I say "the wrong way round" I mean it ;)

I wish. Plan is to do this in very small chunks of 1-2h hours at a time, I think it'll take me 1, maybe 1.5 years to complete. I've done Cape Town to London via Dubai in the same plane, that took just over 3 months.