1

I took the Arica - La Paz bus a few months ago, it's no more unsafe than any other route. Nice scenery too.

Not sure about hotels that offer pickups but I don't think it's really necessary. The taxis are safe enough if you take an official one. Just make sure your accommodation has 24 hour reception. Bolivia is not as dangerous as you might think. Though do watch out for petty theft, pickpockets, thieft by distraction etc

Americans don't need a visa to enter Chile. Just make sure you don't have any food with you, or declare any snacks you do have.

2

1. Most of the better hotels and also the most popualr backpacker ones (Loki etc) offer airport pickups. As #1 says the official airport taxis are safe enough. They wait right outside arrivals and have "Aeropuerto" on the side. There is also a price list (in Bolivianos not dollars!) to the various zones where you leave the airport building. Let your hotel know you will be arriving late.

2. La Paz - Arica is the easiest, best road and also superb scenery. If you are doing one of the tours in Uyuni area you can do a 3 jeep day tour which takes you to the border for a connection to San Pedro de Atacama. The train from Uyuni only goes as far as the border now 1/2 days a week. Entering Chile usually straightforward as long as you dont have fresh fruit, veg, meat or dairy products, coca leaves etc. Processed packaged snacks (biscuits, chocolate bars etc) not a problem, if in doubt show the officials.

3

Awesome, this is great advice, thanks so much everyone!