Ah, August! The month named to honor Emperor Augustus…
For a long time I had the feeling that there was something else to Jesus and the renderings to Caesar, doing research I found that there is lots of stuff that appears on the web that seems to be tainted by agendas. However, I do know a place were all this can be sorted out: where else but the Straight Dope? 
My suggestion (and someone else must have come with it, so I want to know about them and take a look at their work) is essentially that Jesus threw a monkey wrench to the Roman taxation system, and this was one of the reasons the Romans decided to get him, not much evidence, I grant it, but years of reading about the history around the gospels tells me that many things that ended up as important in the gospels, like being the one, overshadowed some seemingly mundane, but not so pointless actions.
So how, in essence, did the Romans do taxation?
http://school.discovery.com/lessonplans/activities/payup/
-Working Romans paid tax collectors a portion of their earnings.
-The tax collectors paid a portion of what they collected to the republic’s senators.
-The senators provided (somewhat) for the poor, while keeping most of the tax money for themselves.
(The more things change…)
So, how to counteract that? Especially since open rebellion will destroy you? Find a way to limit the earnings of their tax base, therefore: less taxes to Rome: I think I see that in Acts:
*Acts 4:32: “All the believers were one in heart and mind. No one claimed that any of his possessions was his own, but they shared everything they had. 33With great power the apostles continued to testify to the resurrection of the Lord Jesus, and much grace was upon them all. 34There were no needy persons among them. For from time to time those who owned lands or houses sold them, brought the money from the sales 35and put it at the apostles’ feet, and it was distributed to anyone as he had need”. *
I have the suspicion that well to do Christians had (ahem), more needs than others, and they in reality did not suffer as monks did later, (Aside: I do have a beef on how many, by their actions today, show that this was not sanctioned by Jesus, although he never mentions that, the acts of the apostles imply that that is indeed WWJD)
I do think the constant encounters with the tax collectors had a background of a nasty growing awareness, by the local tax collectors, that some rich citizens of Palestine were beginning to show up empty handed, and publicans were demanding some explanations, I think many suppers were organized to discuss those matters:
Mark 2:16: “When the teachers of the law who were Pharisees saw him eating with the “sinners” and tax collectors, they asked his disciples: “Why does he eat with tax collectors and ‘sinners’?””
Have you noticed how many big talks with tax collectors were stopped by miracles or by big shows of faith?
I can see that famous line of: “Render therefore unto Caesar the things which are Caesar’s and unto God the things that are God’s.”
In a different light: Yes, render to Caesar, but you can render less if you join us…
Still, it was an example that needed to be eliminated; later, on the road of taking Rome, Christianity “forgot” that part of the history, easy to do when it is you who depend on the tribute of others now.
I think the movement had in it, a growing threat to the roman taxation system, and Jesus or the apostles (similarly like Ghandy and the Salt Vs the British Empire in the 20th century) found a way to hit the Roman Empire were it hurt, and all that, without taking arms. The question (and part of the debate) is: if it was pure happenstance or a brilliant move.
(Or, there is nothing to see here, don’t pass go, don’t collect 200 shekels… (What do you mean there were no silver denarius in Palestine when Jesus was there!?!?) http://www.nd.edu/~ndmag/au2001/bible.html )
And I might as well find about this since it could be relevant: Was Judas actually a former tax collector?
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