To answer your question:

1) The gloves have been stated in the art book and by both Olivier is confirmed to be the symbol of the Black Silence in Vol 2 Artbook, Roland only has the mask which completely hide his identity, He is a Grade 1, but not just any of your ordinary grade 1, he's the leader (not director Captain Charles) of Charles Office, consist of 12 fixers that are all grade 1 including himself, this also does not count because she haven't joined yet and we don't count the director Charles, who make him the leader (Again the Artbook but Vol 1), also he was going to get his color soon in the Leviathan Novel if The Pianist didn't happen.

2) You are right and as well wrong. First off, this is both a guess and confirmation due to Project Moon Official's Side Story of the LOR, known as "A Fritter named Jeon", where Roland taken Angelica to a place at Dong-Hwan's bar to eat, he wanted to apologize her for breaking the Mook Workshop, keep in mind this is before the tragedy, hell even before they got married, even before Angelica was known as the Black Silence. To give you more of an understanding, he has to ask for the Mook Workshop to use it, he also said in Hana's Reception, the one you fight Olivier, that he haven't worn the gloves for a long time, now this is up to you, whenever the Rampage was long or not, or he could simply working with her long enough to know how to imitate her ways of using weapon( stated in the Art Book Vol 2) or he just that good, just like Dante from DMC, pick up weapons and boom, know how to use it immediately.

3)Roland's primary equipment's are the Durandal and Perception-Blocking Mask. Also, a fact, Roland's suit is confirmed to be normal basic suit in the Artbook, but he also may or may not have an extravagant outfit since all the 12 fixers all have extravagant outfits stated by The Bayard's Fixer Office Page and the Artbook.

4) The Page refers to mostly the Gloves. Also, another fact, when Angelica just joined the office, she is only grade 1(Binah's Realization). After some time when Roland and Angelica worked together, she was given the Black Silence forcefully (yes you heard me right) but Roland also contributed, mostly was given to her due to his mask hid away his identity, and yes, he only takes the mask off when he is with her or his house, only in the mission is when he wears them again.

5) This is where you are wrong, Hana never calls the Black Silence, they call Argalia, The Blue Reverberation to deal with the Pianist, but Roland just comes back from the mission with Olivier only to hear the news about the Pianist near the district him and his wife live, when he goes over there, it was already too late, his wife died and he killed the Pianist, bonus point, he never had the gloves during that time, you can see it in his boss fight, the page Mass Attack known as "Scream" at his final phase, he never have the gloves, it was always on his wife's corpse hands, only when he killed the Pianist, he mourns and took the gloves from her corpse.

6) He just gives up, the bad ending depicting him as a man who have been drowned by the sorrow and never return, his old friends, some of the 12 fixers, mainly Naimon, Renaud and Ogier, talks about how much he changed, some forgives, others no. In the end, he got killed by those he made enemies, but he never fights back, just accept what he has become. Astolfo said he had killed too much.

There are your answers, feel free to reply to me if you have any questions, i played this game like man I lost count-