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Feh. People will be telling you you're crazy all the way to Tierra del Fuego and all the way back. They'll have all sorts of reasons. Try not to take them too seriously, particularly if they've never done the trip themselves. "Concerned" friends are the worst, followed closely by locals who tell you that the residents of the next town/state/country will harvest your organs for profit and drink your blood for fun.
I did skip Sao Paulo, having heard lots of stories of bike-jackings. But I rode thousands of km all over Brazil as a whole, despite the intense swarm of rumors about piano wire beheadings. I made a point of riding through Tegucigalpa during daylight, not at night, but I had no real reason to stop there anyway. I skipped Caracas for the same reason.
I carried (and frequently used) a cover, a high-security lock and chain, and some cables to secure helmets and riding gear when I left the bike for hours on end...which I did a lot of. Once I left it in an unguarded lot for a week while I walked through Torres del Paine, and it was undisturbed when I returned. I wouldn't do that in London or New York, that's for sure--or in my own driveway.
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