You have a MA CCW.......wow.......they are not easy to get. No you are not thinking too much. I use to live NYC (enough said regarding CCW or even owning). You do need to use caution. The decision to CCW is personal and along with the ownership/ccw right is an even greater responsibility. As a certified instructor I say....The day you stop worrying about those things is the day you should surrender it....because that is when you will get careless. Keep up the thinking. Caryy when you feel the need to...and be safe.