Regarding your issues, I have issues (well, issue): Travel in South America does not require visas for an American. It is very easy to travel here, we've had no problem for the last 6 months.
Bolivia charges a reciprocity fee upon entry for all Americans. Other than that we haven't paid anywhere else. That said, we've done land border crossings since Colombia. Brazil, Argentina, and Chile WILL charge a fee when you fly into them internationally.
We've also travelled for 5 months through the poorest countries of South American with an iPad, MBA, 2 iPhones, 2 Kindles, and $2,000 in camera gear. This doesn't cause stress, you just don't flaunt these things openly in public.
I however agree with the sentiment of not working while travelling.
That's great to hear about traveling here as an American. I was only going off what other Americans had told us, they had said it was harder than it needed to be. We have just about the same gear you're traveling with, and I totally agree; just don't flaunt it around in public and you're fine. We haven't had any problems at all (so far!) with that.
Bolivia charges a reciprocity fee upon entry for all Americans. Other than that we haven't paid anywhere else. That said, we've done land border crossings since Colombia. Brazil, Argentina, and Chile WILL charge a fee when you fly into them internationally.
We've also travelled for 5 months through the poorest countries of South American with an iPad, MBA, 2 iPhones, 2 Kindles, and $2,000 in camera gear. This doesn't cause stress, you just don't flaunt these things openly in public.
I however agree with the sentiment of not working while travelling.