My Hebrew is a bit rusty, got stuck on Proverbs 14:14, and particularly the second part of the verse, וּ֝מֵעָלָ֗יו אִ֣ישׁ טֹֽוב׃ How do I translate, וּ֝מֵעָלָ֗יו correctly in the context of this verse and how does the second part of the verse relate to the first part?
This is indeed a difficult verse.
From his ways
he will be filled*
[the one of] backslidden heart
but from on it/him
[will be filled]
a good man.
The only real difficulty here, as the OP points out, is ומעליו. As written, it contains four words: and-from-on-him/it. It's possible to understand מ and על together as meaning "on account of" and then gap דרכים ("ways") from the prior line:
but on account of [the ways of] him
[will be filled]
a good man.
However, this is a difficult reading with an excess of ambiguity afforded by gapping both the verb and the object of the prepositional phrase (sans pronoun) from the prior line. Accordingly, many commentators have suggested an emendation to וממעלליו, meaning “and from his deeds”.
וממעלליו טוב לב
and from his deeds a good man [will be filled]
This yields a much clearer text, and the origin of the MT reading can be understood as haplography, dropping one each from the מ and ל pairs. Furthermore, the words דרך (way) and מעלל (deed) are essentially synonymous in this usage, making them good candidates to stand in parallel; they are also elsewhere paired (e.g. Jer 17:10). For all of these reasons, the emendation may offer the most plausible reading.
This answer is indebted to: Bruce K. Waltke, The Book of Proverbs (Grand Rapids: Eerdmans, 2004), 608 (note 30).
*The verb שבע, lit. "to be filled/sated", is being used in the sense of "to be requited", which can carry connotations which are either negative (as in the first line) or positive (as in the second line).
My Hebrew is more than just 'rusty' so take what I say with a pinch of salt; I'm much more confortable with Greek.
So, since the Greek of the verse helped me understand the Hebrew a lot, I'll share what I think is a correct parsing and translation of the Hebrew.
and/but-with-on/in/concerning [i.e.thing(s) proper to]-him
OK, so first of all, you have classic and very detectable Hebrew parallelism. Parallelisms are often of great help when trying to understand tricky passages.
So in English we might translate this:
The man of an aberrant heart is filled with his ways: but a good man with the things [within] himself.
The LXX has:
τῶν ἑαυτοῦ ὁδῶν πλησθήσεται θρασυκάρδιος ἀπὸ δὲ τῶν διανοημάτων αὐτοῦ ἀνὴρ ἀγαθός
He that is haughty of heart is filled with his own ways: but the good man with his thoughts (or, intentions/motivations).
I gather from this that the meaning, stripped of all possible Hebraisms, is as follows:
The fool [Vulg. stultus/'fool'] is only concerned with how he acts, whereas a good man has consideration for (even) his intentions.
See Matthew 5:28; Mark 7:21.
The Vulgate appears to be taking מעל as a preposition meaning 'above:'
...et super eum erit vir bonus
...and a good man shall be above him.