Deuteronomy 32:44-52 KJVS
“And Moses came and spake all the words of this song in the ears of the people, he, and Hoshea the son of Nun.  And Moses made an end of speaking all these words to all Israel:  And he said unto them, Set your hearts unto all the words which I testify among you this day, which ye shall command your children to observe to do, all the words of this law.  For it is not a vain thing for you; because it is your life: and through this thing ye shall prolong your days in the land, whither ye go over Jordan to possess it.  And the Lord spake unto Moses that selfsame day, saying,  Get thee up into this mountain Abarim, unto mount Nebo, which is in the land of Moab, that is over against Jericho; and behold the land of Canaan, which I give unto the children of Israel for a possession:  And die in the mount whither thou goest up, and be gathered unto thy people; as Aaron thy brother died in mount Hor, and was gathered unto his people:  Because ye trespassed against me among the children of Israel at the waters of Meribah-Kadesh, in the wilderness of Zin; because ye sanctified me not in the midst of the children of Israel.  Yet thou shalt see the land before thee ; but thou shalt not go thither unto the land which I give the children of Israel.”
Moses being the Law giver could not go over Jordan unto the land our Heavenly Father had given the children of Israel for a possession.
We can see why Moses could not Passover the river Jordan in Numbers Chapter 20.
Instead of sanctifying God by speaking unto the Rock, he smote the Rock twice.
I believe there is a deeper level to why Moses (who is the Law giver) could not go over into the promised land which was given for a possession for the children of Israel.
Let’s take a look at the Law, Grace, and Faith, and how it is related to our true crossing over into the Promise Land, Eternal Life.
Romans 6:14-23 KJVS
“For sin shall not have dominion over you: for ye are not under the law, but under grace.  What then? shall we sin, because we are not under the law, but under grace? God forbid.  Know ye not, that to whom ye yield yourselves servants to obey, his servants ye are to whom ye obey; whether of sin unto death, or of obedience unto righteousness?  But God be thanked, that ye were the servants of sin, but ye have obeyed from the heart that form of doctrine which was delivered you.  Being then made free from sin, ye became the servants of righteousness.  I speak after the manner of men because of the infirmity of your flesh: for as ye have yielded your members servants to uncleanness and to iniquity unto iniquity; even so now yield your members servants to righteousness unto holiness.  For when ye were the servants of sin, ye were free from righteousness.  What fruit had ye then in those things whereof ye are now ashamed? for the end of those things is death.  But now being made free from sin, and become servants to God, ye have your fruit unto holiness, and the end everlasting life.  For the wages of sin is death; but the gift of God is eternal life through Jesus Christ our Lord”
Yes indeed, free from death only by the gift of Eternal Life given to us by our Heavenly Father through His only begotten Son Jesus Christ.
Being made free from sin and its wages, we can become servants of God and His righteousness.
Matthew 5:5-6 KJVS
“Blessed are the meek: for they shall inherit the earth.  Blessed are they which do hunger and thirst after righteousness: for they shall be filled.”
Filled with righteousness and given an inheritance that is Eternal which is the true Promise Land, we understand through the form of doctrine, which is our Heavenly Fathers Word, Jesus Christ, that the Law is good (1st Timothy Chapter 1 verses 8 through 11) but it cannot take you over unto the Promise Land, which is Eternity.
Galatians 3:18-29 KJVS
“For if the inheritance be of the law, it is no more of promise: but God gave it to Abraham by promise.  Wherefore then serveth the law? It was added because of transgressions, till the seed should come to whom the promise was made; and it was ordained by angels in the hand of a mediator.  Now a mediator is not a mediator of one, but God is one.  Is the law then against the promises of God? God forbid: for if there had been a law given which could have given life, verily righteousness should have been by the law.  But the scripture hath concluded all under sin, that the promise by faith of Jesus Christ might be given to them that believe.  But before faith came, we were kept under the law, shut up unto the faith which should afterwards be revealed.  Wherefore the law was our schoolmaster to bring us unto Christ, that we might be justified by faith.  But after that faith is come, we are no longer under a schoolmaster.  For ye are all the children of God by faith in Christ Jesus.  For as many of you as have been baptized into Christ have put on Christ.  There is neither Jew nor Greek, there is neither bond nor free, there is neither male nor female: for ye are all one in Christ Jesus.  And if ye be Christ’s, then are ye Abraham’s seed, and heirs according to the promise.”
Hiers according to the Promise, and this Promise is only given through Jesus Christ who is the Seed of Abraham, and it is by our Faith in Jesus Christ, we become one in that Seed, and are given Grace by our Heavenly Father who sent us the Seed of Eternal Inheritance, His only begotten.
Romans 4:13-16 KJVS
For the promise, that he should be the heir of the world, was not to Abraham, or to his seed, through the law, but through the righteousness of faith.  For if they which are of the law be heirs, faith is made void, and the promise made of none effect:  Because the law worketh wrath: for where no law is, there is no transgression.  Therefore it is of faith, that it might be by grace; to the end the promise might be sure to all the seed; not to that only which is of the law, but to that also which is of the faith of Abraham; who is the father of us all,”
In conclusion, Moses could not lead the children of Israel into the Promise Land, as the Law itself cannot give you Eternal Life, however Joshua who was a strong type for Jesus Christ was chosen to go forth instead.
Joshua 1:1-5 KJVS
“Now after the death of Moses the servant of the Lord it came to pass, that the Lord spake unto Joshua the son of Nun, Moses’ minister, saying,  Moses my servant is dead; now therefore arise, go over this Jordan, thou, and all this people, unto the land which I do give to them, even to the children of Israel.  Every place that the sole of your foot shall tread upon, that have I given unto you, as I said unto Moses.  From the wilderness and this Lebanon even unto the great river, the river Euphrates, all the land of the Hittites, and unto the great sea toward the going down of the sun, shall be your coast.  There shall not any man be able to stand before thee all the days of thy life: as I was with Moses, so I will be with thee: I will not fail thee, nor forsake thee.”
The Law is not dead, and our Heavenly Fathers grace is very much alive, and only by your faith and the gift of grace that has been given to you, you can cross over and claim that Promise. (Ephesians Chapter 2 Verse 8.)
From Moses, to Joshua, and from the Law unto Grace through our Faith in Jesus Christ, we will Cross Over.