Chop-chop

So in Acts 16, Paul has Timothy be circumcised "because of the Jews" who lived in the area. So in essence, Paul has Timothy go through a heck of a lot of pain simply to appease the legalists. Am I reading this wrong? Why does it seem that legalism always gets the final word. I know that Paul's heart was to not be a hindrance to anyone so that if it meant getting Timothy chopped then so be it, but I just have a hard time with this. I guess this is like any situation where you conform to surrounding culture in ways that aren't harmful to your relationship with Jesus in order to help in your ministry to that culture. I guess its just weird to me because on one hand it appears that Paul appeases the legalist culture but then later on in Galatia he speaks out so much against circumcision and makes a mockery of why don't you chop everything off if that is the way to holiness. Paul is a weird character. He seems like the type of guy who would have a beer with the bar crowd and then turn around and speak of the abomination of alcohol with the super conservatives. Is this the idea of being all things to all people that he writes about in Corinthians? At what point do you stop? Should a person ever have customs or practices? Or are we called to be willing to be whatever to whomever? Coming full circle, I guess its just weird to me that Timothy had to go through circumcision. No wonder he felt timid in his ministry - to get in he had to cut off part of his manhood.