Is it simply speculated supply and demand, or is there a simpler approach?

As stated above I simply just went with umbrella insurance and called it a day.

I win in all situations even if it burns down.Also with this option we do not have to worry about taxes (which hurt every time we have to pay them) or maintenance.

After agreeing on a purchase price, I would simply add a commission fee to the price of the house and the buyer would provide the funds (purchase price + commission fee) to buy the property.

There is good and bad to this arrangement: The good is that the money is simply listed as owner investment to the bank and on taxes.

These can all play a factor in getting the best win-win deal. :)

At $6000/yr income that's 40% CoC.Am I missing anything or does this look like a win-win?

@Matthew Morganstein With the exception of a few places (TO, Vancouver, Calgary, {maybe} MTL & Québec), I'm not convinced wholesaling works well here in Canada simply, due to the relatively small market size, and state of present market conditions.

Would it be best to just contact an administrator on the website to see what the requirements are, write down the classes, and simply complete them, and go from there?

If you win an auction in Cook County it is because several dozen other smart guys did not want it.