it is an exceptionally good question.
My wife and I, have rececently been introduced to the whole hebraid roots teaching, but not by any man. For us it came complete out of nowhere.
At the minute we struggle, not just cause it is quite 'odd' but because the only other messianic believers we know are the ones we know online. Britain is quite small, and there is not really a large jewish population, which means synagogues are few and far between in our land.
We have started to study the feasts, but it is one thing knowing the theory about them, and another to know how they are celebrated practically. Another question we struggle with is related, and that is our relation to either keeping or not keeping the Torah. We cannot find any cut and dry answers. It is difficult as the NT is written to a primarily Jewish audience. And Paul appears to have been so misrepresented that hammering through 2000 years of baggage is proving mentally difficult.
However all that aside, the month of Elul has been one of introspection and my wife is looking forward to yom kippur (in a strange kind of way).
Steve
p.s. i am sure this does not really answer the question but gives you an insight into the difficulties faced by christians with no jewish background at all (in practice or theology)