3 Guys, 1 Trip, Many Questions. [Canada 12/13)

Ahoy fantastic community,

I'm hoping that a few of you can chime in on this post to help some dudes out with the unknown. I commend you if you make it through the whole thing, but I'll put a TL;DR at the bottom in the hopes of more feedback.

So myself and 2 of my best friends are sitting in Brisbane, Australia concocting this grand plan of coming to Canada, and making use of at least half of a 2-Year working visa. At present we're in the process of aquiring said visa. We have not yet booked flights, or even settled 100% on a departure date; Mainly due to a few unknowns. Travel Insurance is a little vague at the moment also. I understand Canada requires us to have health cover when we come over, as to not leech your system as foreigners. Completely understandable. But if someone has experience in doing so could you please chime in? Do we get travel insurance then transfer to health insurance through a Canadian provider?

A little about us...
My name's Dion. I am 25 and work in Film and TV - I've heard from other Aussies who are in the Industry and have gone across the pond that getting work in Vancouver is relatively easy.
Brad is 27 and is a commercial electrician. Not sure on the recognition of trades internationally.
Lucas is 26 and is a commercial refrigeration mechanic. Don't you guys just put all your stuff outside to chill anyway? I think he'll be s**t outta luck trying to find work...
We've been saving this whole year. We really wanted a cash bed to make things easier on us getting over and getting things done throughout the working holiday. I think it's safe to say, at this stage we're each looking to depart Australia with $10 000ea.

The working holiday...
We've built this whole trip around the snow. We're boarders and have our own gear. Our sights have been set on Big White for some time, the combination of good snow, intermediate runs, village size, and ease of finding accom. and employment make it the most attractive option at the moment. That much is concrete. We would like to be living and working on the mountain for this upcoming season (2012/13). We DIDN'T want to come to Canada to meet other Aussies. Although I've just started hearing that Big White is the new Whistler. :(
Our rough plan at the moment involves flying into Vancouver from Sydney flying Air NZ. Then once our feet are on the ground we would perhaps stay a week and figure out how to get out to Kelowna. Ideally we would like to be the proud owners and operators of a motorvehicle for the duration of our stay, so this would be our first port of call.
We kinda really want what we call a fourby/four-wheel-drive/4x4. I think you guys call them SUV's. A Jeep Wagoneer would have us elated... Haha! We've been hunting on the Canadian websites getting an image of the market over there, and what we can expect. In a perfect world we'd like to fly over and already have one in out sights.
So with a car sorted, we would then be driving out to Kelowna/Big White to get us some accomodation and a job. The thing that really governs the time we leave Australia is the employment part. We can leave anytime this year if we had to. But realistically, we would like to leave as close to the time that would offer us the best chances of getting a nice job as close to when we land; We don't want to eat into our money sitting around waiting for interviews to start.

Brad wants to leave in mid August, as he thinks this will be the best time to get a job based on what he's heard.
I want to leave in late September/early October, as I've heard interviews start a month before first fall - So mid October?
We really don't know what the best time to head over is, so this is BIG question at the moment, because we would like to book our flights. Would it be possible to line something up from over here in Australia?

So after that, the next thing to attack would be accomodation.
If we get in early enough, and our luck is overflowing enough, we would love to stay in a Chalet/Chateau.... We call them Holiday Homes. We have heard from a few people that owners rent them out to folks over the winter. I've looked on a few websites, and wow - Nice, but expensive. Could we get something cheaper by being on the mountain and having a look around ourselves? We would really like to be living on the mountain. We don't want to have to commute to and from Kelowna each day. What other styles of lodging is there to suit 3 blokes over a winter? Apartments, houses etc?

After that I guess it gets cushy. We'd work out the season on the mountain, learning things from other people about the country and preparing to make our next move. Which is of course, to move to Vancouver for a bit. But seeing as though that's almost a year away now, the planning can wait on that front...

So that pretty much concludes the in-depth write up of our trip. I applaud you for getting this far. Below are some succinct TL;DR's for you to answer...

TL;DR

1) What do we do with regard to mandatory health insurance?
2) Do you think foreigners purchasing a car for a country-wide working holiday is a good idea?
3) When is the best time to arrive on the mountain to offer the best chances of finding a job you want?
4) Is it possible to organise employment internationally, and is it worth it?
5) What accomodation can we expect to land into - Ideally we want a Holiday Home.

Alright guys. Please post if you can enlighten us in the slightest, it would be greatly appreciated.

Cannot wait,

Dion.