Simcha challenges many Christian traditions in this series. But I don't see him challenging any Christian theology, the Word in the Scriptures. Rather he looks at Christian traditions to try to determine where they came from; whether from Scripture or outside sources. I have heard some of these questions before so I'm not sure is Simcha is offering anything new or just compiling these ideas in a single source.
Here are some examples. (1) We arbitrarily celebrate the birth of Jesus on Christmas which was chosen because it is the birth day of the pagan sun god Mithras; episode 5 'Selling Christianity' (2) Jesus is said to have walked on water on the Sea of Galilee. But the Sae of Galilee is not named in the Gospels. Did it occur elsewhere, episode 4 'The Lost Voyage of Jesus'. (3) Simon of Perea lead a massive Jewish rebellion shortly after Jesus's birth in response to Herod's mass murder of Jewish children. His follower's regarded him as a Messiah, a role he privately confirmed. Simcha looks at whether he was misguided or whether a dual Messiah concept is consistant with Scripture; episode 2 'The Messiah Before Jesus.
I think Simcha's goal in this series is essentially to purify Christian tradition taking a fresh look at what is solidly founded on Scripture and what as crept in over the centuries. I personally believe that much has also been lost over the centuries and that the message of Jesus is much richer than we know. In other words, I think Christianity has been simplified, or dumbed down, to make it easier for the masses and new converts to understand. Simcha's narratives support this opinion. I espcially like the episode "The Lost Voyage of Jesus" because a simple question of 'where it happened' leads to a much more powerful interpretation of the life of Jesus.
Knowing the truth, we may not change how we worship God. Chistmas is an essence an arbitrary choice for Jesus's birthday that let's us remeber the events in his life over the course of a year. But shouldn't faith be founded on truth.