Hi There!!
I just traveled Bolivia, Peru, Ecuador (flight to Cancun) then overland to Guatemala and Mexico. It's totally do-able. Word of warning...bus rides are very LONG (and sometimes a little scary).
I didn't have any issues with border crossings. My biggest recommendation would be to LEARN SPANISH if you don't already have a grasp on it.
You can check my blog at a rediscovered life on wordpress if you want more information. Or email me privatly through here with specific questions. I would be happy to help.
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