You might want to focus more on just studying scripture.
To be clear, Jesus openly admitted to working on the sabbath, which is a transgression of the law, but answered His accusers that "The Sabbath was made for man, and not man for the Sabbath. Therefore the Son of Man is also Lord of the Sabbath.”
The Bible doesn't say that Jesus never transgressed the Law, but says that He was without sin and always did what was pleasing to the Father.
16 For this reason the Jews persecuted Jesus, and sought to kill Him, because He had done these things on the Sabbath. 17 But Jesus answered them, “My Father has been working until now, and I have been working.”
18 Therefore the Jews sought all the more to kill Him, because He not only broke the Sabbath, but also said that God was His Father, making Himself equal with God. 19 Then Jesus answered and said to them, “Most assuredly, I say to you, the Son can do nothing of Himself, but what He sees the Father do; for whatever He does, the Son also does in like manner."
If you're unable to understand the how and why of Jesus' ministry, you'll never understand your liberty in Christ or the opposition between self righteousness and the righteousness of faith. I won't tell you how to live, but the law was given to confine everyone under sin and can not perfect righteousness.
18 For on the one hand there is an annulling of the former commandment because of its weakness and unprofitableness, 19 for the law made nothing perfect; on the other hand, there is the bringing in of a better hope, through which we draw near to God. Hebrews 7:18-19
21 Is the law then against the promises of God? Certainly not! For if there had been a law given which could have given life, truly righteousness would have been by the law. 22 But the Scripture has confined all under sin, that the promise by faith in Jesus Christ might be given to those who believe. 23 But before faith came, we were kept under guard by the law, kept for the faith which would afterward be revealed. Galatians 3:21-23
The Hebrew festivals are indeed rich with meaning pointing to Christ, but when you've recieved Him, they've already met their purpose.
When I was young and Catholic, I wanted to be a Jew. Now I'm old and having been born twice, I'm content with what the Lord created me to be.