Happy birthday Chicago !
Here is an old thread that is somewhat related .
http://forumserver.twoplustwo.com/sh...Number=7637184
Generally speaking , if your opponent's range is ~ the top 50% of hands , then your re-raising range should be ~ the top 25% of hands . If you believe your hands plays better post-flop than the average hand your opponent would have , then you should consider re-raising . I find the biggest weakness amongst heads up players is that they seldom re-raise . Against a player who raises or folds his button , then you should be more inclined to 3-bet as his range is fairly wide . This means that against a player who raises the majority of his hands on the button , then it's imperative that you re-raise more than 25% of the time .
You may also negate your positional disadvantage by giving him less than 2:1 odds on the call .