teedledee: In your case, the rule logic needs to be fixed. Only one rule can match and the first one that does is the one that gets run. Also, is there a reason why you are using two rules for this? If you want multiple actions to be applied to the same file, why not just use multiple actions in the rule?
gregjsmith: Sorry to get back to you late on this. If it is an Applescript, unless you throw an error, the script is considered to have run successfully. If you want the rule to be re-run on failure, you need to indicate that failure to Hazel by throwing an error.