I have long felt that the timing and location of Jesus’s coming, together with the missionary work into Gentile regions made perfect sense from historic and strategic points of view. He was sent into the dominion of the Roman Empire, one of the most powerful and extensive empires of all time. They had made travel easier with a system of roads. The early churches in Macedonia, Greece and Asia Minor were on the crossroads of major trade routes to and from the known world. God in His infinite wisdom had a good marketing plan.
The witness of the spirit is all anyone needs to determine whether Paul was sent by Jesus to preach to the Gentiles,
The early Church were all out of Israel (the 3000 were numbered, but later as Gentiles, were never counted) and while they understood the core of those things in the Feast Days, the Law and the prophets, those things which Christ had come as promised to fulfill with his teaching, death and resurrection, the Gentiles did not have that background, this is why God sent us a Torah expert. The rest were all able men but of secular occupations and learning, Paul was a Hebrew scholar.
Paul tended toward arrogance, he was impressively scholastic, if he had been writing only secular books he would now be celebrated with the greatest minds of world history, and this is why he says God did not heal his ‘thorn in the flesh’ (I think it was his eyesight but we’re never told)
Years ago watching the movie Jurassic park, I remember commenting on the scene where the billionaire owner talking about his grand-kids being lost, when he said, who better to bring them back safely through a dinosaur park than a dinosaur expert. That’s what he did with Paul, he gave us someone that could help us get up to speed quickly with what we needed to know and not get lost in the legal minutia that was now to be written in our hearts (spirit) and not for temporarily blinded Israel, (rejected flesh)
The Church is not under the law, or under the Feast Days, or in what day we worship, however never think the Sabbath is no longer Saturday, but worshiping on Sunday for the church is just fine, that’s what our Torah expert Paul explained to us. Jesus said if you love me you’ll keep my commandments, yet understand the entire sermon on the mount was about the impossibility of ever keeping the law, this was for Israel first, but they rejected it, and he made it clear they had to reject it first (before) the Gentiles could be brought in,
Equally important, it was through Paul’s writings that we’re told of things to come about the second coming and the falling away, and that man of sin being revealed,
The Church came in by the spirit, which by a natural accounting is very nebulous even to our spiritual understandings (the law is written in our hearts) Israel is blinded now temporarily, and for the world it is a complete mystery to the natural mind, it is even foolishness. Paul said we would see that day approaching,
These are some of the very things the spirits at work in this world, principalities and powers, wickedness in positions of authority and also operating as wolves in the fold seek to diminish the understanding of, always remember that Satan is the accuser of the brethren, and his time accusing Paul is not over,
You may find it refers to another thread, which if you find, may relieve the confusion.