In response to your first question, and as a person experienced with web community planning & development, I'd like to advise you follow a few golden rules.
- Entice people to join your website community. (Whether this is through something like special offers on services, prizes, or just great information isn't that important. What is important is that you offer them something worth their time of signing up and joining.)
- Make the content on your website original and more importantly, useful.
- Reward members of the community for actively participating and referring others to join. (This website is a great example of "rewards" with badges / points.)
- Poll your community on ways to make it better, and listen to the feedback!
- Be an active member in the community by helping new members and building report.
The real thing you're striving for in any community is "member loyalty" and a raging fan base. It's definitely worth taking some time, thinking about your target audience in depth and planning how to reach them. Trust me that this will pay off long term!
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Regarding your second question, the first few things that come to find would be to contact some of the big named realtors / brokerages in the city and try and get them on board. A second idea, which would take a bit of work, would be to search for terms like, "Homes for sale in Toronto." Make a note of who comes up first on Google and ask them where they get most of their hits from.
Hopefully some of this is of use to you - cheers,