Phew!
E,
I always start and end my rides in Peru as that has been my first home for 30 years of this short life, so I can't really help you with what is the best licensing, etc. I'm not sure what other countries require insurance besides Peru and Argentina, both of which you can purchase at or in the town right before the border. Both are quite cheap.
I would research well the Venezuela to Brazil route... I've read that it is a little rough. There is a decent road across the Amazon from Manaus, but it is only a "summer road"! DO NOT attempt it between November and May! If you need to go that way during any of those months you can just put aboard a river passenger boat as the Madeira river follows the road (or vs/vs) all the way to Humaita (where it is paved) or a little farther to Porto Velho. From there you can go east to Peru, or south thru Brazil and everything is paved.
If you are going the Venezuela to Brazil route... how to you plan to see any of Peru??
About visas, that will depend on your nationality, so it is probably different for you. Both Brazil and Bolivia set their visa costs for US citizens in retaliation for what the US charges them (about $130 each), but I don't know for you.....
I visited Ireland 5 years ago. Wife and I arrived in Shannon and caught a bus to Innis, then hitchhiked to Doolin. Wonderful people and countryside! We stayed in youth hostels and wee inns. Went out to see the islands, then up to Galway (stopping on the south side of the bay to watch an automotive Hill Climb Rally. Where are you from?
Toby  
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