I played DitV with some good friends who are able to roleplay fine, but they were really taken aback by some of the aspects of the game. I was mastering and found myself trapepd into old reflexes. So...

 - Don't hesitate to force your players! The rulebook says that it's fair game. If they don't want to be convinced of something that's a conflict. Set the stakes and play it! In my first game, i had a lone player facing the mayor of the tone, very agressive, who wanted the pc to obey his every orders. The player was very surprised when i answered his "i'd never do that" with a handful of dice and a "prove it"
 - Present the characters with potential conflicts very early. As soon as they arrive in the community, swamp them with demands. Don't play all demands as conflicts but the way your town is written should give you enough hints as to what conflicts could arise
 - Don't heistate to change the setting. If your players feel uncomfortable in the Olde West, play prohibition, or mafia, or wherever the players can find a strong community united against the outside.

i'll give only a link to [the forge forum for lumpley games][1], where you'll find resources, pre-written towns and idea about settings...

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Edit just to add, the "Don't keep secrets" rule is **essential**. You don't play DitV as another game where the mystery must be uncovered.

  [1]: http://www.indie-rpgs.com/forge/index.php?board=44.0