I think Mark 10:24 provides the key to understanding Jesus’ comments about the “rich” – he is criticizing those who “place their trust” in wealth, and not in God. It is not being rich per se that is to be condemned; it is forsaking God for the sake of riches that is to be condemned.
That translation of Luke 14:33 is questionable, for starters. The Douay-Rheims Bible, for example, translates it as,
“So likewise every one of you that doth not renounce all that he possesseth, cannot be my disciple.”
The accompanying commentary says, “we … must be in that disposition of soul, as to be willing to renounce, and part with every thing, how near or dear soever it may be to us, that would keep us from following Christ.” The key words are “willing to”.
Reading the preceding verses suggests Jesus is taking about priorities – ie, putting him above everything else in one’s life, including family and even one’s own life (v.26). Jesus is not telling his disciples to give away all their possessions.
In Luke 14:33, Jesus cannot literally be telling his all disciples to give away all their possessions, because firstly, other Scriptures suggest otherwise. I’ve already mentioned Mark 10:24, but also consider Luke 19:8, in which the tax collector-turned-disciple, Zacchaeus, tells Jesus he has given away “half “ of his goods to the poor. How come Jesus didn’t say to him, “That’s not enough – if you want to be my disciple, you must give away all your goods to the poor”?
Secondly, it would simply make no sense at a practical level for all of Jesus’s disciples to give away everything they own. What is to be gained by everyone being reduced to abject poverty? Who on earth would want to join a religion requires everyone to live in poverty? That sounds like a surefire recipe for turning potential disciples away, not attracting them!
How are disciples expected to survive if they give away all their possessions? How on earth would married disciples be expected to raise families, for example, if they give away all their possessions?
How could the Church even exist as an organization if everyone in it has no possessions and no money?
How could a disciple practise his trade or profession if he has to give away all his possessions?
Jesus said he wants us to have life “abundantly” (John 10:10) – does living in the misery of abject poverty sound like having life "abundantly”?
I’m not aware of anywhere in the gospels where Jesus demands poverty and/or celibacy from his disciples. However, in the Catholic Church, a tradition developed in which some disciples are expected to, in a sense, give away all their possessions – every Catholic priest in the world must take a vow of poverty (and celibacy). But clearly, these demands are not expected of all disciples.