Notice in v1 of acts 2 that they were all in unity waiting on God. This is the first requirement for God to work, a oneness of spirit with Him and each other. There was no wind, only the sound of a wind so those that "breathe" The Holy Spirit on people based on this wind are in error as there was no wind in the room. The Holy Spirit made His presence known through using cloven tongues that were like a fire. Note: Like a fire and not an actual fire as there was nothing to burn (which a fire requires).
There is no statement He actually entered them. He did not need too as He was already in them or they would not have been followers of Jesus and marked as such by The Holy Spirit being in them. To baptise is to immerse. So there was not entry of The Spirit in them or it would have been called something else and it would have been noted that the Spirit has entered them. His presence was in that room and they were immersed (baptised) in His presence.
The anointing does not enter you. You may feel the presence of The Holy Ghost working through you affecting your body as He works the Will of God. But He does not enter you to anoint you. It is not necessary, as the empowerment is from Him as you declare the Will of God and He is already in you marking you as belonging to Jesus as well as your authority in The Kingdom.
I note that Jesus did breathe on the disciples before He Ascended into heaven but it was symbolic to mark the coming of The Holy Spirit and to show them as belonging to Him and not to authorise and empower them for ministry. This was done later at Pentecost. Any person breathing on people to impart a gift or anointing is doing so incorrectly as they cannot give the spirit to mark them as belonging to Jesus because that occurs at Salvation and they cannot give what is not theirs to give anyway.
The gift of tongues came forth from those in the upper room because The Holy Spirit descended on them. This was not angelic tongues but tongues of other people's languages so that they could understand the message when they were preached to by the apostles (Acts 2:4-12). Remember they were being commissioned to spread the good news of Jesus throughout the world and it was necessary for people in other cultures and of other languages to be able to understand them. So the disciples were given this gift of speaking in their own language but being understood in the language of the person they were speaking too. I have heard of this actually happening in the 20th Century but it is rare and I believe the true gift of tongues will always have someone there it is directed too who will understand it.
Demons can do a similar thing. Note that there is a demon called a scrambler demon, who can make a person hear the opposite of what is actually being said. This is to start division between people. So always make certain you actually heard what the other person said when there is a problem of communication.
Anyone teaching that tongues other than this type were present at Pentecost is in error.
These 'tongues' grasped the attention of peoples from different races and cultures who could not understand how these Jews could speak in their language. Some thought they were drunk with wine so Peter got up and preached in his own tongue to all that were there and all the different nationalities understood what was said in their native tongue. So another mark of the tongues that occurred at Pentecost is that it was not incomprehensible to the speaker as they were hearing what was said in their own native language which they spoke every day.
Note that the gift of tongues was given to promote the Gospel not to prophesy or edify people. It was to show forth the marvelous works of the Lord Jesus.
The Gift of Tongues at Pentecost was one of the manifestations of The Holy Spirit but there were other manifestations all designed to encourage people to believe in Jesus as Lord and Saviour (v21). Signs and wonders are for the promotion of Jesus, His Gospel and The Kingdom of God not to give the church or any of its members prestige or importance. In fact being used to express these in your life should drive you to greater humility.
In v22 Peter declares that these signs and wonders were a continuation of what Jesus did in the midst of them in spite of which He was put to death. Peter then declares Jesus was raised from the dead and that the signs and wonders He did continues in the followers of Jesus. In v23-36 Peter explained whom Jesus was in terms of the Messiah in the Old Testament and people responded and wanted to know what to do to follow Jesus.
His response was that they should be baptized in the Name of Jesus (so they would identify with Him and repent of any baptism to and worship of other gods they had worshipped before) and accept what Jesus had done at Calvary (the remission of sins, redemption etc.), and that they would also receive The Holy Ghost.
3000!! I repeat 3000!! Of all different nationalities believed what was preached, were baptized and became followers of Jesus from that one demonstration of signs and wonders at that one sermon (v41).
The unity continued as did the Miracles and daily worship (v42-47) and would do so as long as they followed the teachings of Jesus. So why do we not see the same thing happening today? The answer is simple. We are not following Jesus as we should.