Fair enough question.
I don't think a modern day Jesus would be spending much time with the Pharisees. I take a look at individuals such as Mary Magdalene as being examples of the people that Jesus reached out to.
I think we're fortunate enough to have people who do actually believe in the Gospel and do live their lives in accordance with Jesus' teachings. The ones I personally tend to admire and identify with are the missionaries.
I do not believe that Jesus was or is stupid or blind. Quite the contrary; when I finally converted (as an adult) I'd have to say that it was the more intellectual aspects of Christ's ministry that finally won me over. Our lord and savior was not and is not a fool. Nor was he or is he a wimp.
Would Christ embrace socialism? Seems to me that Jesus would have a hard time embracing a de facto religion that has as one of it's apparent tenets the replacement of God with the state.
On the other hand, I do think that Jesus would (and is) working awful hard to seek out and turn individuals towards grace.
My personal answer to the question I posed to you last night. FYI.