If I decide to move to a new unknown location and the new outside location tile drawn has a road that doesn't connect to my current one, can I still move or do I have to stay until a new tile is drawn in the next turn that may have a connecting road?
It will always connect to your location as this game does not have the same limitations to placement like games such as Carcassonne or Age of Steam. The only concerns it that a road connects to the road you are leaving your tile on. If the new tile has other roads that dead end and don't connect to another road, that's fine.
Still not clear on this. If I'm in the outside halftrack tile and I place the supply truck tile, the supply truck tile road doesn't connect to the halftrack tile, therefore I don't think I can enter it. Do I have to backtrack now?