Character: Ramza Beoulve, Final Fantasy Tactics
Memories available to swap: OH BOY, WHAT FUN WE WILL HAVE, PICK YOUR POISON but mind the spoilers:

FAMILY ISSUES:
-Ramza's father dying in withering sickness as Ramza clasps his hand and hears his dying words
-Ramza seeing an innocent/hostage get shot by his allies to preserve the honor of his knight order in front of her brother Delita's eyes
-Ramza being called all but a bastard child by his older half-brother for distrusting them
-Having his sister be pretty much the only person to trust him within his family
-Like, anything relating to his sister's kidnapping shortly thereafter
-Ramza killing his demon-possessed older brothers in miserable and agonizing self-defense

FAITH ISSUES:
-Ramza culling impoverished dissenters
-Ramza's first realization that culling impoverished dissenters is, like, a really bad thing to do
-Ramza entreating a high cardinal for aid
-Seeing the high cardinal become a demon and having Ramza slay it
-Encountering a high confessor on charges of high heresy for murder of a cardinal
-Seeing a whole bunch of other people become demons
-Seeing his kidnapped sister become possessed by a beautiful fallen angel
-No, wait, it revealed its true form, it's another horrifying skeletal demon

MISCELLANEOUS ISSUES:
-Ramza saving the life of an enemy squadron leader he doesn't yet recognize as such
-Ramza re-encountering the squadron leader on the battlefield and leaving as mutual allies
-Ramza battling a certain red Chocobo in the wild, only to see her surrender, have him spare her life, and tend to her wounds personally when he realizes she's gravid
-Ramza encountering a very bewildered Cloud Strife after activating a strange machine
-Ramza accidentally ordering a golem to CRUSH KILL DESTROY a good friend
-Ramza walking into a bar and ordering a glass of milk