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So I would say "detachment" in the sense of a cold, hands-off attitude toward all things, is bad; but "detachment" in the sense of putting Christ, always, radically first, is good.
Does that make sense?
How much we want to smooth the edges off of this one! It is indeed a hard saying. One of the hardest!

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Wikipedia:
1. Emotional detachment, in psychology, refers to "inability to connect" or "mental assertiveness"
2. Detachment (philosophy), a philosophical state

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SOME, OCCASIONAL detachment is needed in this world or we would go crazy.
Also detachment from unsavory friends or people who lead us to do bad is NECESSARY. Sometimes the latter detachment is from some family and/or friends and may have NOTHING to do with the Lord.

Putting Christ first is always good but Christ would be the FIRST to say "help each other" and that might mean having to deal with those from whom we would detach ourselves with all due speed.
It's MOST unpleasant to have to deal with the down and out, drunks, addicts, over-eaters, manipulators, jerks, fools and aholes, but they may be the ones who need us the most. THEY may be our God-chosen path to the Lord.

In other words, detachment isn't one or the other. We need our good Lord to help us discern how we can follow the straight and narrow and how we can help our fellow human beings. Detachment from THEM may not be what the good Lord wants us to do.

You ALWAYS make sense, Mrs. Don-o.
Of course, maybe I wouldn't want to cross you before you had your first cup of coffee in the morning. :o)