Yeah, all of those questions were tumbling through my head.
In a lot of ways it's appropriate to make the following comparisons:
1. Jesus = Moses
2. Judas = Pharaoh
Another question -- suppose Judas had not killed himself. Would Jesus have forgiven him post-resurrection? Would we be justified in comparing Judas and Paul as exemplars of how we choose?
The examples of Judas, Pharaoh, and Paul (among others) suggest that "will" is not everything -- when necessary, God can and does intervene. But then, the fact that God makes Himself known to us, and also answers our prayers is proof enough that there's more to the equation than simply free will.
In Romans 5 and 6, Paul goes through a similar analysis with regard to the law:
What shall we say then? Shall we continue in sin, that grace may abound? God forbid. How shall we, that are dead to sin, live any longer therein? Romans 6:1-2
Let no man deceive you by any means: for [that day shall not come], except there come a falling away first, and that man of sin be revealed, the son of perdition; Who opposeth and exalteth himself above all that is called God, or that is worshipped; so that he as God sitteth in the temple of God, shewing himself that he is God. II Ths 2:3-4
The beast that thou sawest was, and is not; and shall ascend out of the bottomless pit, and go into perdition: and they that dwell on the earth shall wonder, whose names were not written in the book of life from the foundation of the world, when they behold the beast that was, and is not, and yet is. Revelation 17:8