Originally Posted by SimpleSimon
I would advise buying the most displacement you can afford. It is nice to have power on tap when you need it. If you buy a small displacement bike, you will want more later power later.
I second this, especially if you are going to do any 2 up.
Shaft/belt or whatever final drives are a matter of personal choice. You really can't beat a shaft for low maintenance, and you did mention something about less than ideal roads. Belts don't like sand & gravel.