It occurs to me that one of the reasons that I am not good at debate is that I don't think particularly quickly. I am often at a bit of a loss when someone makes what seems to be a reasonable argument but I know it is flawed, I just can't think quickly enough to figure out the problem. Part of the solution may be to determine in advance the most effective responses to various arguments. One issue that I have seen is allowing the opposition to define the terms of the debate.
Example. "You can't be free if you are struggling to survive. You are trapped in a situation that doesn't allow you to be free, therefore the government must provide you with a certain standard of living so that you can do what you want to do".
The problem here is a actually one of definition. The opposition has defined freedom to mean "the ability to do anything you want" and if we a accept their definition then their argument is reasonable. If we redefine freedom as the ability to make your own choices even if you must live with the consequences then the argument starts to fall apart. If you are struggling to get by then you have the freedom to do the extra to change your situation. When the government steps in they must, by definition, take from others to provide that help, reducing the freedom of those others to advance their own situations.
Taking a bit of time to ponder the definitions that our opponents are using might be the difference between winning and losing the debate. I refer you back to the phrase "assault weapon" which is meaningless but has become a part of the language and is now enshrined in law.