OK for starters, do you want to stay in or around cities and towns, or would you rather be out of town?
Do you prefer your nightlife to be under stars or disco balls?
Do you desire to move to new areas frequently, or stay somewhere months at a time?
Extensive touring or laid back?
Do you have other hobbies/activities that you wish to indulge in other than the occasional glass of wine? ie fishing hiking museums or tours.
Do you want all the modern conveniences all the time, or do you prefer simple life?
Are you going to follow the seasons, or mechanically force your personal climate? (Migrate for weather or run AC and heat extensively)
Get an idea or tell us what you think you want to do, and someone can give you ideas as to how they approached those questions.