I think so. You are one who sees The Law including such things as a tailor unwittingly wearing a piece of clothing with a stray needle in it on the Sabbath, breaking the Law (in Jesus' time, the Oral Law). It wasn't written down until a couple of hundreds years later. What else could The Law mean in Jesus' time? Usually, the Ten Commandments, but that could be expanded to include the first five books of the Bible, or sometimes the entire Torah. We've already gone over what Jesus meant (The Ten Commandments and obedience to the will of God.) It seems in your thought, it also included not only the entire Old Testament, but the Oral Law of Jesus' time. Jesus, however, didn't think much of Oral Law (washing hands, healing on the Sabbath, harvesting grains of wheat on the Sabbath when hungry to name a few).
One of the early Church Fathers put Jesus fulfilling all Law this way: Love God and do what you want. Loving God takes one straight back to God's will and the Ten Commandments. It dismisses things like walking around with a needle in your clothes on the Sabbath.
As far as the Jewish Messiah...interesting points on that. If a prophecy is not fulfilled within a few generations, it is usually considered an error or a false prophecy. Herod's Temple, at one time, had been counted as the Third Temple because of all the renovation and rebuilding taking place, which was the source of the great anticipation for the prophesied Messiah as that Messiah was prophesied to come at the time of the third Temple. Then, when Herod's Temple was torn down, there was a bit of back-pedaling occurring. It was pointed out that Temple sacrifice and rites had occurred during all this rebuilding and renovations and Jewish leaders insisted this technically meant Herod's Temple was still the Second Temple since there had been little or no interruption of sacrifices and services.
Hebrew and Aramaic etymology can be tricky. So, you're right, I cannot help you if it is your belief that Jesus meant more than the Commandments and obedience to the will of God when he referenced The Law.