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ough
I've never properly tried tubeless tyres on any of my bikes so someone with more experience can answer better. I know they puncture less and can have lower rolling resistance. You would need to carry sealant, plus inner tubes as a back up. Tubeless tyres do tend to be very tight to mount onto rims. Personally I'd just use tubes inside proper touring tyres, keep an eye on pressure and routinely check them. You can find tubes and patches in most countries.
Yeah it's romantic to have unplanned stops, for sure, but that can turn to frustration if you get really stuck. One friend attempting Cape Town to Cairo ran into that issue with visas, couldn't enter DRC after multiple attempts (probably for the best), waited two months in Rwanda/Uganda while trying, got frustrated, flew to India instead, cycled until kidnapped by some Indian rebel group, was released unharmed and then featured on Indian national TV with the headline ticker: "John the Canadian is safe!" He was a bit naive by planning to cycle solo across DRC, so probably wasn't careful enough in general.
TL/DR: Do your visa homework, do your rebel research.