Hi @WDOWEARY, that’s an interesting question that you brought up. Actually I didn’t know that Satan entered Judas as well haha.
Though I don’t have a direct answer to the Enemy (as a fallen angel) entering Judas, I do have one where a non-evil spirit enters the believer.
Do you not know that you are a temple of God and that the Spirit of God dwells in you? (1 Corinthians 3:16)
I will put My Spirit within you and cause you to walk in My statutes, and you will be careful to observe My ordinances. (Ezekiel 36:27)
Many other verses also support that the Holy Spirit fills the believer and the gift of tongues is a proof that the Holy Spirit dwells in them.
All of them were filled with the Holy Spirit and began to speak in other tongues as the Spirit enabled them. (Acts 2:4)
I believe it stands to reason that if your body is the temple of God, and the Holy Spirit dwells in you, it will not allow another evil spirit to dwell in the temple of God.
If memory serves, I don’t think any believer after the crucifixion has been possessed by any evil spirits.
As a new creation, we have full authority over the forces of evil.
The seventy-two returned with joy and said, “Lord, even the demons submit to us in your name.” He replied, “I saw Satan fall like lightning from heaven. I have given you authority to trample on snakes and scorpions and to overcome all the power of the enemy; nothing will harm you. However, do not rejoice that the spirits submit to you, but rejoice that your names are written in heaven. (Luke 10:17-20)
In that day, because the believer did not have the Holy Spirit dwelling in them, they are susceptible to demonic possession.
Not sure if this adequately addresses some parts of your question.