Automatic generalization algorithms are not yet a complete solution, they still often make decisions a careful cartographer would abhor. Natural Earth has a good background article on how their approaches to generalizing features, a multi-step manual process. Axpand claims the Swiss Topography Office had an 80% success rate with automatic generalization when using their software with topographic maps.

You've mentioned in a few responses that you don't like the 'bony' geometries produced by many automated solutions, could you explain what aspects of the data you'd like to retain? Are you interested in positional accuracy of the results, or more in the aesthetics of the result? That will help give us a sense of where a solution might lie.

Automatic generalization algorithms are not yet a complete solution, they still often make decisions a careful cartographer would abhor. Natural Earth has a good background article on how their approaches to generalizing features, a multi-step manual process. Axpand claims the Swiss Topography Office had an 80% success rate with automatic generalization when using their software with topographic maps.

You've mentioned in a few responses that you don't like the 'bony' geometries produced by many automated solutions, could you explain what aspects of the data you'd like to retain? Are you interested in positional accuracy of the results, or more in the aesthetics? That will help give us a sense of where a solution might lie.