Yes you can allow free or paid ad listings (or a mixture of both), and customers can upgrade to featured listings later if you set this, however there is no specific option as you describe. You could also offer coupons via the
AppThemes coupons plugin, for a discounted rate if you wanted to offer an introductory price. Ad listings are not automatically separated by location, but there is an advanced search functionality in the category view sidebar as shown on the
demo site, which allows search by location. Thanks.