@disillusioned: Gehenna he meant it is a place of eternal conscious torment instead of the annihilation
I think it depends on the context. In the context of Matthew 5:29-30 I think he’s talking that it is better to cut your own arm/eye etc than go down to the literal place of Ben-Hinnom, where according to Jewish lore, people did worship other gods like Baal. Ben-Hinnom was according to some contemporary texts inhabited by a large number of “foreigners” in that day that likely practiced foreign religions, likely because of poverty prostituted themselves etc.
Baal, Molech and other nearby that still believed in Proto-Yahweh in that day were often demonized by Jews as having child sacrifices (propaganda not supported by any archeological evidence) but they also seemed to have “fun” practices like temple prostitution and alcohol.
Whenever Jesus is translated to hell, he refers to Gehenna or the valley of Ben-Hinnom as a literal place, which likely means he sees it as a place where you get to do “immoral things” and separate yourself from the Jewish god. Basically Jesus is saying it is better to mutilate yourself than “go down to the hood” and have fun with “those people” and everyone knew what he meant.
There are only a few places where Jesus refers to Sheol/Hades both for Lazarus and the Rich Man parable and the resurrection and which is a place commonly accepted as darkness/silence after death (a pre-heaven)
I personally think hell gets more of the Orthodox Jewish context of a place where you go practice another religion without (the single unified) God. That is still the closest you get to a Jewish concept of what Christians describe as hell today, you go do bad things and then you are tormented by the consequences and your conscience. Orthodox Jews don’t believe in eternal torment, even go as far as saying they don’t know what happens after death, therefore we need to do our best now. I think that is what Jesus in context of a Jewish teacher would have taught. The Hellenistic views of hell as a literal place of torment only come later as Christianity starting as a Jewish sect integrates more and more teachings from Greek and Romans.