First, I'm the owner of a kayaker's hostel in Pucon. Pucon Kayak Hostel was designed to put lots of kayakers under one roof and provide logistics solutions.
1.What is the boating season in chile?
Nov/Dec is best creek season. Futa will be high then. But norther stuff like the Seven Teacups National Park is perfect. There are over 70 clean waterfalls including Garganta del Diablo (whirly bird drop aka Throat of the Devil). Pucon guarantees clean waterfalls and multiple sections to run.
Jan- sunny, northern region is drying but Maipo is always good. Pucon still has lots of options, and by Futa region is getting better by the day.
Feb- Pucon is in peak-season with tons of travelers. It's like July but since Pucon is so plentiful there are still the base runs: Palguin sections, Trancura, Maichin, Liucura (III), Fuy, San Pedro...
Futa- is optimal.
March- is great for Futa and most people are gone. Some of the base runs around Pucon are gone but two others open up at lower levels: Middle Fuy and Truful Truful.
If you an advanced intermediate i think Jan Feb is your time. If you're a creeker you're probably going to like December best.
2.Roughly, How much would a trip cost for that entire season?(Flight, lodging, food, gas, etc.)
Flight- check expedia. Fly closer to Pucon via Temuco and cut out northern bus rides. About $1700-1800 to Temuco from Denver.
You can click to look at the Pucon Kayak Hostel lodging
and kayak rental rates.
Chile has nice restaurants slightly cheaper than Colorado and mom pop empanadas and fried eggs places for around $3 a meal. If you shop around you can find cheaper hostels than PKH but the cool part is being able to show up and hang with international kayakers.
3.Should I bring my boats or rent down there?
Boats rent for $20/day. Flying can be done and can miss. It's getting tougher and we're currently investing thousands to ship 12 new creek boats for this reason. If you can get a new kayak down there then you can sell it or I'll even bartar your lodging and food at the end of your trip (if it's in good shape).
4.Is there a decently sized crowd so that I could boat with them?
Yes. Pucon (anytime) or Futa in late Jan to Feb
5.Where is the best place to be?(Pucon, Futa, etc.)
I'll recommend my own PuconKayakHostel.com
Futa for all-inclusive RxRivers is great. Or do it yourself goto Cara del Indio.