Yesterday, I wrote up an article explaining why I cannot recommend any commentaries on the Gospel of Matthew on the Olivet Discourse in Matt 24–25.
That being said, I mentioned that I have benefited from commentaries, in this case with respect to Matthew 24–25. (Commentaries are not my first resource I consult. I first interpret a text based on my own skill set of hermeneutics. Then I will consult journal articles and monographs, and lastly I might consult a commentary, only then to be often disappointed by a lack of substantive exegesis.) But there have been a few commentaries that have had some nuggets on the Olivet Discourse. I do not necessary agree with the presuppositions or methodological approaches of these commentators, but here are a few:
Matthew: A Commentary on His Handbook for a Mixed Church under Persecution by Robert H. Gundry, 2nd edition, Eerdmans. Though I take issue with much of his redactional-critical comments.
Matthew 19–28 Vol 3 by W. D. Davies and D. C. Allison, T&T Clark.
Ulrich Luz’s commentary in vol 3 in the Hermeneia series.
Craig Keener’s Eerdmans 1999 commentary on Matthew is cautiously helpful for the socio-historical context, but lacks substantive discussion on the Greek text.
Other popular commentaries such as by France, Nolland, and others, I find just repeat themselves (which is very common in the genre of popular commentaries), not to mention come from a dated Greek understanding of the verb system and/or lack substantive linguistic analysis on the Greek text.
Again, one will benefit more from monographs and journal articles on Matthew than commentaries—that is where you will find the red meat. This can be said of any book of the Bible.