Automated legal matter and answering machine

I am trying to implement a web application that will allow users to define rules and ask questions to see if allegations are legal or illegal in accordance with a set of rules. The areas that I mean will be the rules for small communities or clubs.

For example, a valid rule set contains rules:

Only cars with valid registration tags may park anywhere indefinitely.
Cars without valid registration tags may only park in a visitor spot for up to 3 days.

And then someone asks "Can I park my Honda here?"

The system will try to answer by first following the tree of questions and answers similar to:

"Is a Honda a car?"
    =>Yes
        "Does it have a valid registration tag?"
            =>Yes
                "Yes"
            =>No
                "Are you parking in a visitor spot?"
                    =>Yes
                         "Have you parked in that spot for more than 3 days?"
                            =>Yes
                                "No"
                            =>No
                                "Yes"
                    =>No
                        "No"
                    =>Define "visitor spot"?
                        "A visitor spot is a parking spot. A parking spot is spatial rectangular area of asphault with a width of 8 feet and a length of 15 feet with a variation of 1 foot. It has either another parking spot or a curb adjacent to it. It has the words "Visitor" painted on it. It ressembles <img>."
                   =>Define "parking"?
                       "Parking is the act of placing a vehicle within the spatial area of a parking spot. The state of a parked image ressembles <img>."
            =>Define "valid registration tag"?
                "A valid registration tag ressembles <img>"
    =>No
        "No"
    =>Define "car"?
        "A car is a 4 wheeled vehicle weighing less than 3 tons."

The user selects an answer on each node, and the system asks the next question according to the answer, until a node sheet representing the "final" answer is reached.

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