1) Why didn’t Maedhros’ ‘repentance’ of wanting the Silmaril last?
He wanted to leave this whole mess behind him, but in the end he just couldn't
let go. The Oath, the Curse, all of the horrible battles -- you can tell
Maedhros is just sick of it. But for those same reasons, he couldn't give
up, he couldn't let go of what he had pursued for so long.
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?
Imprison them where? I just don't think that's the way they did
things. Maybe it would have worked.
2) Was the Silmaril really the source of the prosperity of the people of
Sirion?
Yes, at least symbolically.
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?
The sons of Feanor have a rightful claim. Perhaps they should give up
that claim to atone for the kinslayings. Let's call the Silmaril a
national treasure and keep it in a museum for all to admire and enjoy.
The museum will be located in Valinor.
4) When all was said and done, were the Silmarils a blessing or blight to
Middle-earth?
A blessing. A thing of beauty is a joy forever,
right?
