1) you are assuming when really you have no way of knowing how ‘repentive’ Judas was. The word there is ‘repented’ not ‘regret’.
See, you are taking the translation of "repented" here in the purely religious sense we use the term today. But in common usage this word meant not some formal repentance but a simple turning of mind. This is why, if you were to check Liddell-Scott (the premier Greek to English Dictionary), both the translations of "repent" and "regret" can be found. Also, "to feel sorrow." It doesn't automatically refer to some form of interaction with God like our modern perceptions of the word "repent" presuppose.
2) “But true repentance towards the Lord brings the Spirit of God upon the scene.” Maybe I’m mistaken but ...Judas’ death was before the outpouring of the Spirit at Pentecost.
Again, Victory, we are getting lost in semantics here. When I say "brings the Spirit of God on the scene," I am
not referring to the baptism of the Holy Spirit. I am referring to the presence of God, such as comes upon people when they receive Jesus in their hearts, and they suddenly feel like the weight of sin is being lifted off their shoulders.
So, He went to the chief priests and elders saying “I have sinned...”
:) The issue here is to what extent did he communicate his sin
to God or simply complain to the Pharisees that they had led him to sin. If I say to you, "I sinned," that does not necessarily mean I have repented unto God. It simply means I am communicating to you that I recognized I messed up somehow. So too was this the case in what Judas was saying to the Pharisees. His communication in verse 4 was to them, not God.
Again, “what is that to us?”
Do you think God would have that same response for Judas “What is that to Me?”
If he had gone to God, no. But again, Victory, you are ignoring the elephant in the room. If you believe he went to God, repented before Him, and entered into right relationship with Him, receiving forgiveness for His sins, why would he then have turned around and hung himself?