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For question #1, Warrax has linked the right thread. Add your items to the $ED82E4 list. Just make sure to adjust the loop like assassin suggested which is right now for 10 items, the CPX #$000A at $C39834 and $C39860. If you got more than 16 items you would even relocate that list and just change the CMP $ED82E4,X  at $C3982D and $C39859. I think that is all there would be to it.

For question #2, you'd need to relocate this code and add entries to the middle fork, the one who compare old and new relics. There would also be a JSR to change at $C39EF8. The more elegant way would be to relocate the code at end of bank $C3 where you have free space.

Code:

Determine whether to trigger Reequip in Relic menu
C3/9F5C:    20F293      JSR $93F2      ; Define Y...
C3/9F5F:    B92300      LDA $0023,Y    ; Relic 1
C3/9F62:    C5B0        CMP $B0        ; Unchanged?
C3/9F64:    D009        BNE $9F6F      ; Branch if not
C3/9F66:    B92400      LDA $0024,Y    ; Relic 2
C3/9F69:    C5B1        CMP $B1        ; Unchanged?
C3/9F6B:    D002        BNE $9F6F      ; Branch if not
C3/9F6D:    803A        BRA $9FA9      ; Reequip: No

Fork: Compare old and new relics
C3/9F6F:    A5B0        LDA $B0        ; Old relic 1
C3/9F71:    C9D1        CMP #$D1       ; Genji Glove?
C3/9F73:    F037        BEQ $9FAC      ; Trigger if so
C3/9F75:    C9D0        CMP #$D0       ; Gauntlet?
C3/9F77:    F033        BEQ $9FAC      ; Trigger if so
C3/9F79:    C9DA        CMP #$DA       ; Merit Award?
C3/9F7B:    F02F        BEQ $9FAC      ; Trigger if so
C3/9F7D:    A5B1        LDA $B1        ; Old relic 2
C3/9F7F:    C9D1        CMP #$D1       ; Genji Glove?
C3/9F81:    F029        BEQ $9FAC      ; Trigger if so
C3/9F83:    C9D0        CMP #$D0       ; Gauntlet?
C3/9F85:    F025        BEQ $9FAC      ; Trigger if so
C3/9F87:    C9DA        CMP #$DA       ; Merit Award?
C3/9F89:    F021        BEQ $9FAC      ; Trigger if so
C3/9F8B:    B92300      LDA $0023,Y    ; Relic 1
C3/9F8E:    C9D1        CMP #$D1       ; Genji Glove?
C3/9F90:    F01A        BEQ $9FAC      ; Trigger if so
C3/9F92:    C9D0        CMP #$D0       ; Gauntlet?
C3/9F94:    F016        BEQ $9FAC      ; Trigger if so
C3/9F96:    C9DA        CMP #$DA       ; Merit Award?
C3/9F98:    F012        BEQ $9FAC      ; Trigger if so
C3/9F9A:    B92400      LDA $0024,Y    ; Relic 2
C3/9F9D:    C9D1        CMP #$D1       ; Genji Glove?
C3/9F9F:    F00B        BEQ $9FAC      ; Trigger if so
C3/9FA1:    C9D0        CMP #$D0       ; Gauntlet?
C3/9FA3:    F007        BEQ $9FAC      ; Trigger if so
C3/9FA5:    C9DA        CMP #$DA       ; Merit Award?
C3/9FA7:    F003        BEQ $9FAC      ; Trigger if so
C3/9FA9:    6499        STZ $99        ; Reequip: No
C3/9FAB:    60          RTS

Fork: Set to open Equip menu
C3/9FAC:    A901        LDA #$01       ; Reequip: Yes
C3/9FAE:    8599        STA $99        ; Set indicator
C3/9FB0:    60          RTS

For question #1, you lost me at "adjust the loop" (I also read Assassin's post and it didn't help). It took me 40 minutes just to find and add my items to the end of $ED82E4 using a decimal to hex converter (for the right ID numbers).  LOL.  I only added two items to the list.  Can you tell me exactly what code to change to make the game recognize 12 items instead of 10?  I am guessing this is the loop you are referring to at $C39834 and $C39860, but I don't know what to modify. It all looks like another language to me!

I haven't tackled #2 yet, but it looks like I might break something attempting it.  I might just get rid of my beefed up glove and replace it with something else!