I'm setting up a real estate website that sends an email to a user notifying them when a property meeting their specifications is uploaded.
Any ideas how I can do this in drupal 6/7 ?
Take a look at subscriptions module also and especially at this tutorial. I think this is a much simpler approach.
Just speculation here, but I'd have a bunch of CCK/Fields and Taxonomies on your property content type. Then I'd put those same fields/taxonomies on the User objects (in 7 you can do this directly, because users are fieldable, but in 6 you would use something like Content Profile)
Then you would hook into the saving/updating of your property content type (most likely using a combination of hook_nodeapi in 6, hook_node_insert and hook_node_update in 7 and hook_form_alter) to compare the fields/tags on the property to users with the same or similar tags/fields and then send those users an email.
If you have large number of users/properties, you'll probably want to use hook_cron to batch process the recently updated nodes instead of doing them on demand. Also, you should be sure to store which properties a user has been notified of to avoid duplicates.