Based on my experience of monasticism, and adapting some of its core concepts to my private life as an oblate, I’d like to address your three points:
1. the same psalms at the Office every week, over and over and over again,
Not entirely. The calendar is dotted with memorials, feasts and solemnities; then there are the seasons. Most Benedictines sing the Offices or at least part of them; for most memorials the psalms are the same but different hymns and Gospel canticle antiphons; for feasts or solemnities, the festive psalms are used; for the season, there are seasonal antiphons for the Gospel canticles and for the Sunday Offices. It’s not as repetitive as one may think and in fact some monks I know well would rather it be more repetitive as they often have to sing many of the hymns and antiphons for some Offices only rarely, which makes doing it well rather more difficult. As one says, he has a great devotion to St. Feria
2. the inability to go and be with the poor and embrace them personally,
The poor come to you and you embrace them personally. The Benedictine charism of hospitality means that it isn’t just the well-off professional that shows up at the door for a weekend retreat to decompress. Through the portals of the monastery come the sick, the broken, the addicted, criminal, the homosexual, the divorced, in short, all of humanity’s ills. All will be welcomed as Christ himself, and all will, if desired, have a monk sit and engage with them. Monks have a powerful ability to truly listen; it’s the first word of the Rule, after all! Countless lives have been saved or put back on the right track by monks. A celibate Benedictine monk has given me the best marital advice of anybody including married marriage therapists; my spiritual director literally saved my marriage by speaking, or rather listening, to myself and my wife independently.
3. the sense of being disconnected from the “real world”.
The monks are in the real world. They are in the world, but not of the world. Monks are not blind to what goes on in the world; they read/listen/watch the news; the Abbot keeps them informed, and through their relationships with oblates, their eyes beyond the cloister walls, they are extremely informed of the world and hardly disconnected from it. Use the words “real world” to describe the world outside the walls to a Benedictine and you may get your head bitten off! (trust me on this, I once made the mistake). The cloister is part of the “real world”. It isn’t “cut off” from the real world, but does have a certain detachment from it, and it helps monks be “in the world” but without becoming attached to worldly things.
Hope this helps a bit. Best suggestion is to spend time in a monastery; most have some sort of vocations program that allows you to get a taste of monastic life.