1) Why didn’t Maethros’ ‘repentance’ of wanting the
Silmaril last? If his host was large enough to overcome the people of Sirion
and kill almost all of them, why didn’t he just overpower them and/or imprison
them instead?
Maedhros falls prey to Silmaril-lust and like a junkie, cannot help
himself. That his host would go on a bloody rampage suggests that he and
Maglor are too overcome with desire for that jewel and disregard a repeat of
their father's actions.
2) Was the Silmaril really the source of the prosperity of
the people of Sirion?
I wonder if the jewel really did help them, but it is the light of the trees,
so it could have divine powers.
3) Elwing and the people of Sirion were awfully possessive
of the Silmaril when, technically, Feanor’s sons had a solid claim to the jewel
too. Did anyone really own the Silmarils? If yes, who?
This gets back to the Valar's demand that Feanor hand over the Silmarils after
the trees were destroyed. Ownership of the jewels is a tricky issue, and
one which is hard to answer consclusively. I'll say that the jewels
belong to Arda -- not Feanor, not Thingol and his heirs, not the Valar.
Yavanna made the trees for lighting the world, so but they are not the property
of any one Kindred, or race. (Other than that, the Silmaril is the
Maltese Falcon of Beleriand with all the riff raff competing for it!).
4) When all was said and done, were the Silmarils a
blessing or blight to Middle-earth?
In the end, the Silmarils were the source of pain and suffering, but they did
preserve the last bit of the light of the trees, and thus are vital reminders
of what Arda Unmarred is like. Think of how the Silmaril of Feanor
helps Frodo later on in the Third Age (where the light of the trees blinds
Ungoliant's last offspring). The Silmarils did result in much death and
torment, but they are part of the larger story of the fight against evil and
are thus
necessary.

Nasmith, Eärendil the Mariner