All in all, Proverbs feels like an Hebraic commonplace book, a compendium of disjointed thoughts from varying circumstances. Modern readers unused to aphoristic wisdom writings will be more frustrated than they ought to be. Solomon's frequent juxtaposition of the wise man and the foolish man should be taken to heart, and the warnings against an unrestrained tongue are very appropriate in the age of @pontifex.
In Ecclesiastes, one feels that Solomon is reflecting on his earlier pontifications on wisdom and foolishness, and answering those who deride the search for wisdom as mere vanity. Somewhere I have read the suggestion—and I am sorry I cannot remember where—that this book was meant to be a dialogue or a contrast between the Pious Man of Wisdom and the Impious Man of Learning, and that we have lost the clear division between the two in the text. It would be a worthwhile exercise to parse out the two as a sort of stage play between two characters, Hope and Despair.
This reading seems more sustainable than the more common reading, which has Solomon merely venting his despondency at the end of his life. Too much of the text is hopeful and perfectly consonant with the earlier Proverbs, and one would have to read Solomon here as either bipolar or intentionally mischievous to read all of Ecclesiastes as a text with a unified voice. In Fr. Knox's footnotes, he suggests a number of lacunae in the text, especially where it jarringly jumps from one voice to another.
I am not stopping much yet to read commentaries on these books, but I will note that there is a fragment of a commentary on the beginning of Ecclesiastes from Dionysius to be found online. Apparently St. Jerome wrote a full commentary while intentionally avoiding any earlier glosses, but I have not yet acquired a readable copy. In any case, I find it more invigorating to begin with a direct encounter with the text, and to make use of commentaries only after it has had some time to sink in.
On to the Canticle of Canticles soon!