I believe God is able to convey His meaning without knowing Jewish culture. When God wrote the scriptures, He being all-knowing, knew that there would be millions of Gentiles, who would not have contact with the Jewish people or Jewish books so He wrote it so that all would be able to know what He was saying. Of course that revelation is by the Holy Spirit.
I have listened to multiple sermons concerning the 'eye of the needle'. The theory was that a person must unload their burdens from the camel (stuff they are carrying) and the camel must get on its knees (Humbleness), to get into the Jerusalem gate called the eye of needle. And that was what Yeshua was talking about. But, historically, the gates called the 'eye of the needle' are Arabic and there was no such gate in Israel until centuries later, when the Muslims ruled and conquered Israel. This sermon has been popular and repeatedly passed around. But is not historical or accurate.
We do not have to unload burdens before entering the city of God. That would be a works salvation. We don't clean up to be saved, so even the application is off. We come as we are, and it is God who does the lifting of the burden and the cleaning.
In the 60's and 70's, many Jewish people came to believe on Yeshua through a very dynamic revelation of the Holy Spirit. So, Messianic Jews tend to believe in the dynamic revelation and teaching of the Holy Spirit. Messianic Judaism (MJAA and UMJC) were more charismatic in view. The MJAA is still mainly charismatic (the gifts have not ceased). I am not sure about the UMJC.