Route planning

Do you select routes that your client struggles with? Route planning is essential so as clients gain new learning experience, the problems though are too difficult a route may demoralise your client and too easy a route may become dull and boring. Do you have specific routes that will gradually challenge your client starting with what they can do and then transferring this knowledge into more challenging areas. If I asked you the questions what specific route would you undertake to teach passing stationery obstructions for the first time what routes would you choose? Do you need different routes for different times of the day?