The apparent disagreements of "Jesus" with "Paul" indeed vary depending on which "Jesus" and which "Paul" are considered. If you compare the "Paul" of Romans and Galatians with the "Jesus" of Matthew, you will find strong disagreement on the issue of Law observance -- the "liberal" (more exactly antinomian, i.e. anti-Law) one being Paul, and the Matthean "Jesus" explicitly opposing him, although definitely not from a Pharisaic perspective.
If you compare the "Paul" of the Pastorals with the "Jesus" of Mark, John, or even Luke, you have a completely different set of portraits again: here a very different "Paul" may sound more "legalistic" than "Jesus," but rather about church doctrine and regulations than about the Jewish law, which is already out of perspective.
Actually I think the Pharisaic pedigree traditionally ascribed to Paul (in Pauline literature, only in one passage of Philippians, 3:5) obscures the problem more than it explains it. If we want to understand the real differences between Pauline literature and the Gospels, one of the first steps imo is to forget about the late story of Acts which gives a very artificial picture of Paul, in which it is practically impossible to recognise the author(s) of the epistles...