The T2000 is the higher end model, if you take a close look at the components used on the two bikes. Example, the read derailleur or rims. As far as I know, both the T800 and T 2000 have the same frame but they do have different forks (though both are made of steel). I own a 2002 T 2000 model and have enjoyed it thoroughly.
Yes, both have fittings for front and rear racks, front and rear fenders, three water bottle attachment points as well.
As far as I know, the new Cannondale Tourers have the 26 tooth chainring unlike the 28 tooth it replaced a couple of years ago. That said, when I bought mine I asked the LBS to switch out the small chainring for a 24 toothed righ which was no problem.
Sorry, but cant help with your Canadian dealer question. Hope this helps. Also check out ebay, sometimes these bikes show up listed and for great prices.