This is quite a thread! A full response might require pages, so I will try to limit myself here, primarily by reliance upon Tolkien's own words rather than my own interpretations.
Piosenniel: Orcs had souls.
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"So in this myth, it is 'feigned' (legitimately whether that is a feature of the real world or not) that He [Eru] gave special 'sub-creative' powers to certain of His highest created beings: that is a guarantee that what they devised and made should be given the reality of Creation. Of course within limits, and of course subject to certain commands and prohibitions. But if they 'fell', as the Diabolus Morgoth did, and started making things for 'himself, to be their Lord', these would then 'be', even if Morgoth broke the supreme ban against making other 'rational' creatures like Elves or Men. They would at least 'be' real physical realities in the physical world, however evil they might prove, even 'mocking' the Children of God. They would be Morgoth's greatest Sins, abuses of his highest privilege, and would be creatures begotten of Sin, and naturally bad. (I nearly wrote 'irredeemably bad'; but that would be going too far. Because by accepting or tolerating their making - necessary to their actual existence - even Orcs would become part of the World, which is God's and ultimately good.) But whether they would have 'souls' or 'spirits' seems a different question; and since in my myth at any rate I do not conceive of the making of souls or spirits, things of an equal order if not an equal power to the Valar, as a possible 'delegation', I have represented at least the Orcs as pre-existing real beings on whom the Dark Lord has exerted the fullness of his power in remodelling and corrupting them, not making them..." Letters of J.R.R. Tolkien, letter no.153
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Because Orcs were not "made" but rather were corrupted from pre-existing beings, they would have possessed "souls or spirits". Otherwise, as JRRT goes on to say in the above letter, they would be only puppets animated at the will and direction of their master.
Following the logic of the preceding letter, one might imply that Morgoth, as a being possessing a soul within the framework of Tolkien's sub-created mythos, would also be not "irredeemably bad". But this seems less sure. For here we must examine Morgoth's own nature. In doing so, I again rely on Tolkien's own words found in a little known essay called "Osanwe-kenta" likely written around 1960 and finally published in Vinyar Tengwar in 1998. In this remarkable piece which addresses the nature of "direct thought-transmission", as described briefly at the end of LoTR, Tolkien says the following about Morgoth:
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"Melkor repudiated all axani [laws or rules]. He would also abolish (for himself) all unati [things impossible to be done] if he could. Indeed in his beginning and the days of his great might the most ruinous of his violences came from his endeavour so to order Ea that there were no limits or obstacles to his will. But this he could not do. The unati remained, a perpetual reminder of the existence of Eru and his Invincibility, a reminder also of the co-existence with himself of other beings (equal in his descent if not in power) impregnable by force. From this proceeds his unceasing and unappeasable rage."
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This is Morgoth's nature and it is "unceasing and unappeasable". This at least implies some inability to repent. Indeed the balance of this piece addresses the Valar's hope that Morgoth would repent while in the captivity of Mandos and that his release after having apparently repented resulted from a fundamental inabilility to comprehend his nature.
Boromir's repenting of his actions cannot be equated with Morgoth. Men enjoy a unique position within Tolkien's Legendarium, in that they have greater ability to exercise free will in contrast to the Valar and Elves whose actions are bound up more strictly by the Music of the Ainur which is "as fate" to them. This is not to say that all is pre-ordained for Elves and the Valar, but rather that they are restricted by the broad brushstrokes which make up the story of Arda.