I recently shipped a container to Chile (20 foot I believe) and had the most complex/interesting/involved experience making it happen. I shipped my stuff from my home in Stockton, California to the port in San Vicente. I am in the midst of writing a huge blog about all of the steps and hurdles and expenses involved in moving all my belongings to Victoria, Chile, but haven't finished it. I can answer most questions, though, having just finished the experience ...even moving all of the contents of my container to my new home in Chile.
As per your specific questions:
1. You can pick a 20 foot or 40 foot container. The 20 foot is half the price obviously. I think there are people who split the load of a 40, but I would recommend against it. It is complicated as heck to do the whole move and involving other people would make it more so. Plus customs wants to go through all of your stuff so you have to make sure it's "clean". I wouldn't want to do with customs giving me problems over somebody else's stuff.
2. In terms of which port to ship from, that's just whatever makes sense because of your location. I'm from Stockton, CA and so I used a shipper based in San Mateo/Oakland/Hayward. Whatever is cheapest because the shipper will send the container to your house with a tractor/truck and drop it off there for you to load. You will have about two or three days before he picks it up again to take back to the shipper's yard.
3. Your question about west versus east coast shipping is a good one. My shipper was Gabriel Cunich and the company was Inter Global Logistics. Phone number is (510) 940-7447. He is extremely knowledgable and helped us a lot. You might have to call a few times to catch him. He might tell you the best port and the best shipper. He is Chilean and everything is "a la Chilena", but my wife is in Chilena and we conducted our business in Spanish so that wasn't a problem.
The biggest piece of advice is to be aware of the cost upfront. We paid $4,000 for the cost of the truck to bring/pickup the container from Stockton and then to have it shipped to Chile (Inter Global Logistics). Then we spent another $1,300 in costs in Chile for customs, taxes, the truck to pick up and carry our container to Victoria, Chile, and the payment to a "agente de aduanas" who is a legal official/shipping expert who shepherds your stuff from the port to your new house. So, that's a lot of money to me, but it was worth it to hang on to all my possessions, clothes, furniture etc. which could not easily be purchased in Chile. The quality of our U.S. possessions is much higher than the quality here, plus the personal value of having all of your own things. Obviously, you will be paying more for the truck delivery and pickup of your container if you live in the middle of the U.S. Also, you have to be patient because the whole process takes at least two months and you're worrying about being ripped off at any point or being hassled by the customs agents if they find anything they don't like. We were never ripped off or overcharged perhaps because we speak Spanish, but we worried about it the whole time.
Christian Jutt

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