Judaism is premised on Christ not being the messiah

Yet.

To evangelize Rabbinical Jews (which is as sensitive as evangelizing Muslims), it's important to thank the historical people for preserving the covenant for thousands of years, among which Jesus and all the Church founders were born. The fact that one group said Jesus has done enough to be judged Messiah now, and the other (eventually) said Jesus hasn't done enough to be judged Messiah now, leads to the bridge-building method of dialoguing with Jews about how we would recognize Messiah before he finishes his work. I don't see a Christian eschatology in which we fail to pray for the coming of the Messiah who will rule over Israel and the world, and if he wants a physical temple as Ezekiel 40-48 hints then I'm sure he'll get one. So the issue is the let the Jews, who seek to keep their theology pure of outside influence, find Jesus in that historical theological testimony, because he's there everywhere. Without stumbling blocks, and also without compromise.

1. Actually, in Acts 3-4 the very Jews who called for Jesus's death became hundreds out of the first 5,000 members of your Orthodox Church. I've posted the exegetical proof but I trust you see it on plain reading (I don't think Tradition would interpret it differently than plainly).

2. Yes, dual covenant is contradictory and I've never taught it; Jews are only saved by accepting Jesus, just as the Old Testament Jews were saved by believing in a Messiah to come before his name had been revealed. There are no two covenants of salvation. However, many nations have various national covenants for good or ill in the Bible, and the Jewish people have some of the best and the worst of the covenantal promises, and their preservation is pretty good evidence that they have a national promise from God to remain a people forever just like Egypt has the same national promise from God to remain forever. In fact, Egypt is told by Zechariah that if they reject the Messiah they will get drought, which is similar to what Israel is told. National covenants are not related to salvation by faith proven by works.

So the "chosen people" (not a Biblical phrase), the people of God, were a mixed multitude for two millennia, then mostly Jewish for two, then mostly Gentile for two, which Paul tells us in Romans 9-11 is a brilliant and balanced plan for the world. He concludes with how much greater it will be to see Jews evangelized en masse again (like they were in his day, when Acts 20 21:20 says many myriads in Jerusalem alone were Messianic Jews): he says in fact it means the time of eschatological resurrection is here when that happens.

Side point, circumcision doesn't disregard Romans unless it is used as a work for independent merit. The good works we do, whether they look like Jewish law (e.g. baptism) or not, can only be done in gratitude for what we have received by grace and Christ's merit. There's a lot tied to that but it's tangential to your point.

Overall, you've got it pretty well right, and the issue is only that there are additional facts that open up the context of what is happening. I'm confident Orthodox would agree with evangelism to the Jews of the message of Jesus being God, Christ, and Savior, but those who have been working through this issue closely for the last ~150 years have recognized that much of the work is pre-evangelism, removing the rocks (and stumbling blocks) and watering and plowing up the hard ground. That also includes getting the church "more adequate explanation" as to how we can facilitate what Paul says will happen.

Judaism is premised on Christ not being the messiah

Yet.

To evangelize Rabbinical Jews (which is as sensitive as evangelizing Muslims), it's important to thank the historical people for preserving the covenant for thousands of years, among which Jesus and all the Church founders were born. The fact that one group said Jesus has done enough to be judged Messiah now, and the other (eventually) said Jesus hasn't done enough to be judged Messiah now, leads to the bridge-building method of dialoguing with Jews about how we would recognize Messiah before he finishes his work. I don't see a Christian eschatology in which we fail to pray for the coming of the Messiah who will rule over Israel and the world, and if he wants a physical temple as Ezekiel 40-48 hints then I'm sure he'll get one. So the issue is the let the Jews, who seek to keep their theology pure of outside influence, find Jesus in that historical theological testimony, because he's there everywhere. Without stumbling blocks, and also without compromise.

1. Actually, in Acts 3-4 the very Jews who called for Jesus's death became hundreds out of the first 5,000 members of your Orthodox Church. I've posted the exegetical proof but I trust you see it on plain reading (I don't think Tradition would interpret it differently than plainly).

2. Yes, dual covenant is contradictory and I've never taught it; Jews are only saved by accepting Jesus, just as the Old Testament Jews were saved by believing in a Messiah to come before his name had been revealed. There are no two covenants of salvation. However, many nations have various national covenants for good or ill in the Bible, and the Jewish people have some of the best and the worst of the covenantal promises, and their preservation is pretty good evidence that they have a national promise from God to remain a people forever just like Egypt has the same national promise from God to remain forever. In fact, Egypt is told by Zechariah that if they reject the Messiah they will get drought, which is similar to what Israel is told. National covenants are not related to salvation by faith proven by works.

So the "chosen people" (not a Biblical phrase), the people of God, were a mixed multitude for two millennia, then mostly Jewish for two, then mostly Gentile for two, which Paul tells us in Romans 9-11 is a brilliant and balanced plan for the world. He concludes with how much greater it will be to see Jews evangelized en masse again (like they were in his day, when Acts 20 says many myriads in Jerusalem alone were Messianic Jews): he says in fact it means the time of eschatological resurrection is here when that happens.

Side point, circumcision doesn't disregard Romans unless it is used as a work for independent merit. The good works we do, whether they look like Jewish law (e.g. baptism) or not, can only be done in gratitude for what we have received by grace and Christ's merit. There's a lot tied to that but it's tangential to your point.

Overall, you've got it pretty well right, and the issue is only that there are additional facts that open up the context of what is happening. I'm confident Orthodox would agree with evangelism to the Jews of the message of Jesus being God, Christ, and Savior, but those who have been working through this issue closely for the last ~150 years have recognized that much of the work is pre-evangelism, removing the rocks (and stumbling blocks) and watering and plowing up the hard ground. That also includes getting the church "more adequate explanation" as to how we can facilitate what Paul says will happen.