In answer to your questions:
1a. There is no built in function to allow these additional fields, however you may wish to check out one of our AppThemes marketplace plugins
here which may provide you with the feature you are looking for.
1b. See above.
2a. ClassiPress includes an advanced search functionality which allows you to determine the advanced search fields for your customers to use. You can see this in the sidebar of the category view in the
ClassiPress demo site here, shown as "refine results".
3a. You can allow comments on the ads themselves but this is open to whomever rather than specific groups of people. Outside of that, buyers would use the contact form in the ad page sidebar in order to communicate with the seller.
3b. There is no rating function built into ClassiPress, however there are plans for the
Starstruck plugin to be made compatible with ClassiPress in a future release of the plugin itself. Currently it is not compatible. Thanks.