Taking the parable of the "rich man" in perspective the consideration is that it is very difficult for those who desire riches to enter into the Kingdom. The reason for this is not that Christ Jesus is condemning this man but that when one seeks only and to excess the "fruits of the earth" then placing one's focus on the spiritual is obtunded. there is no sign in the world of spirit stating "rich men not allowed".
A better understanding can be appreciated by learning of what happens at and beyond death to the individual man. At death his life 'flashes before him" in pictures(imaginations) and this lasts about 2-3 days or how long the man could stay awake without sleep in his life.
Subsequent to this he enters into the "soul world" known as kamaloca in eastern thought and purgatory in Christian understanding though I haven't read any delineation of this realm within the Christian church(s) as we know it conventionally.
In this realm, which lasts about a third of the person's life , for example 20 years if the person lived to the age of 60 the soul proceeds backward from death to birth. this is actually the amount of sleep time the person experienced within the life on earth.
In this realm the soul experiences all that he has caused to others or his effect upon others during his lifetime. He experiences what the other felt. It is in this realm that karma manifests as a futuristic experience. By helping a person in distress one feels what he has caused and likewise if the man has punched someone in the nose he will experience this distress of another. this again, can be the precursor to future karmic involvement.
Other matter are brought forth in this realm. For example, if one is a gourmand and loves specific types of food the desire stays with the individual for desire is of the soul, not the physical body which is the corpse of the earth. This desire, if during earthly life, had not basis in spirituality then the gourmand is purged of this desire and suffers greatly until the particular desire no longer exists.
One cannot proceed further into the spiritual world with earthly desires which have to be cleansed in order for the soul to enter into higher realms. All traces of earthly manifestations are purged for this , example gourmand, has no place for fulfillment. There is no earthly food in the heavens.
The soul/spiritual being demands this purging and willingly accepts for he knows that further progress into the higher spiritual realms is obviated until the earth ceases to have effect. Even the cleverness of an inventor of great magnitudes goes through this purging so long as what he has accomplished in his meanderings is earthly not spirit dedicated.
The time between repeated lives, at present, is about 800 years but this is flexible and dependent upon the development of the individual soul and also the development of humanity.
Back to the rich man; it seems it would be difficult if all his predilections are only of the earth but he is not refused the ability to change and gain a karmic fulfillment into the next life.
Yes, there is suffering in the heavens, meaningful within Love.
This does it better ; An Outline of Occult Science by Rudolph Steiner
http://wn.rsarchive.org/Books/GA013/...013_index.html