If by theology, you mean the possible interpretation of "strip away almost everything", while it is debatable whether this particular parable actually means that, it is always accepted that a rich person can give up what they have. This is literally the words of Jesus (Mark 19:16-22), the context in which the parable is given.
Francis of Assisi is an example of one person who made this decision.
Plus takes into account that in text criticism the more difficult spelling is usually the more correct, then rendered into the more common through lapsus calami/scribe error.
The parable of the talents and the connection between investment skill and being blessed by the master show that being rich or good with money is considered a good thing that can be used poorly or toward evil, not simply evil in itself. It is the love of money that is the root of all evil, not that money is evil in and of itself. Money is simply a tool fit for a purpose, as Jesus shows with the miracle of the fish with a coin in its mouth which was used to pay their temple taxes, so that Jesus could keep the legalistic Pharisee and Sadducee busybodies off their backs for a little while longer.
"Render unto Caesar that which is Caesar's." Or something like that.
I don't see this as an issue. There are only so many images to use in a subsistence agriculture society, hence sheep and grain coming up over and over. Sometimes similar images will be used to make different points.
If you want something genuinely difficult, have a look at the alternative explanation of the parable of the talents where the man who does not commit usury is the good guy. One of the gospels (Luke) has additional detail about the "nobleman" who goes off to which suggests this is Herod the Great, (bad guy - see Lk 19:27), so the original meaning is up for debate. Personally I believe that a large part of the point of parables was to spark debate, so we should not assume that the meanings are obvious.
These words eventually became the foundation of Christian charity in an Ancient world that until then despised and rejected the weak and infirm.
Many of our modern day institutions trace their origin to that Christian charity, to those few enigmatic words.
(Peter Brown's “Through the Eye of a Needle” is a great book to know more about this process.)