The transfers from Santiago are very expensive when quoted alone. When we were going to be arriving a day late for the NASJA trip, I was quoted $110pp from Santiago airport to Valle Nevado, and you had to pay that round trip price even if you were only going one way.
Now I'm dealing with
Santiago Adventures on a package deal where the transport costs aren't broken out. Since they run El Arpa and I'm getting a press discount I'm not inclined to nitpick.
I'll respond to Chris C.'s questions because I'm also a "hyper traveler" and his proposed itinerary is essentially a combination of my 2005 and 2007 trips.
Peru: We'll be there 9 days, and if you're going to hike the Inca trail you need 7 minimum. Our extra 2 are for river rafting (which also adds a 3rd acclimitization day in Cusco) and the highly recommended Nazca lines. Without the hike you could hit some highlights in 4 or 5 days. If you want the Inca Trail in July or August you need to reserve it at least 4 months ahead to get specific dates. We barely got reservations for Sept. 1-4 in late May.
Las Lenas: Saturday to Saturday for the hotel/flight schedule and enough time to get a good shot at Marte open.
Other Argentina and Brazil: We had one day Buenos Aires, 1.5 days Iguazu Falls, 4 days Rio. These are the consensus highlights, all popular and easy to arrange.
Chile: I'll know more once I've been there, but since Santiago Adventures runs the El Arpa snowcat skiing, they have package deals where you stay in Los Andes and ski both there and at Portillo for as many days as you choose.
I think 3 days is about right for the lift-served Valle Nevado group. The guy at Powderquest says La Parva's terrain is more challenging, but Valle Nevado gets more snow. They have an
8-day package which also includes El Arpa/Portillo, but like Extremely Canadian is not flexible for dates.
One of the guides from CPG in Alyeska works at Valle Nevado's heliskiing in the summer. Terrain and prices are customized to the interests of each group. For a strong group in exciting terrain plan on about $950 for 25,000+ vertical.
If you go to Chillan, you can chew up 2 days getting there and back to Santiago, which NASJA was going to do by train to minimize cost. I'd recommend flying or spending some of that transit time in the Colchagua Valley wine district. It's also possible to cross the border farther south from Chillan (maybe skiing Pucon also) and go to Bariloche.
But on a "hyper travel" schedule in Chile I think it's best to stay close to Santiago.
My two trips are a combined 5 weeks. If you want to go everywhere ChrisC mentions, I think you need at least 4 weeks.