if you are from the northern US, you won't find chile cold except at high altitudes. i grew up in colorado and i know what weeks of sub freezing temps and high winds are all about. even in furthest southern parts of chile, like punta arenas, it doesn't get nearly as cold as chicago or minnesota or vermont. the ocean moderates the temperatures.
southern chile is more or less comparable to the pacific northwest...oregon, washington, BC, along the coast. lots of rain, but very rarely sub freezing temps...except when you gain altitude to 1500 meters or so. northern chile is kinda like southern california or baja....hot and dry as soon as you get more than a km or two away from the ocean. the central valleys of chile (the valleys between the coastal mountains and the BIG ones) are wine country...like italy, like california. grapes need a long, hot, dry season to mature into good wine making grapes.
my preference is for less sun, more rain, cooler temps, so i'm looking at places like concepcion, valdivia, osorno, puerto montt, calbuco....but i really won't know what i like until i spend more time there....can't wait til january....
this web page may help. it has lots of data regarding temps and precipitation:
http://en.wikipedia.org/wiki/Climate_of_Chile