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Assuming you're an Anglophone (English speaker) I would suggest you live downtown, on the west island, or to the west of Montreal. Anything east of downtown is very Francophone. North and South of the city are mixed.
I haven't been following the real estate market closely but it doesn't appear to be significantly down. Canada has avoided most of the collapse that's happening in the States.
Taxes are much lower off the island and the commute downtown isn't too bad (atleast compared with the commute in DC and Boston). Also housing prices are much cheaper off island. My wife and I bought our home 4 years ago and what be bought on Ile Perrot was in the low $200's while comparable places on island were $350k+,
I would suggest renting for at least your first year in the city. Buying in a market you don't know puts you at a disadvantage. Plus you might end up hating it here and moving somewhere else.
Overall it's a nice place to live. The hardest thing to get used to was the fact that most stores close early here (between 5 and 9 pm in most cases). There are extremely few 24 grocery stores which I greatly miss from when I lived south of the boarder.
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"Every normal man must be tempted, at times, to spit on his hands, hoist the black flag, and begin slitting throats."
--H.L. Mencken
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