in trying to help the only caring woman in his life he made a huge mistake and and he feels he must pay penance by continuing to fall in love with women who have loose screws, and he might feel undeserving of a normal, loving relationship.

Pre-soul did he feel undeserving, though?

I do think there's something to the imprinting. It was his role in life and perhaps that's why its his role in death.

I dunno.