So, what routes and later events could cause characters in the Nasuverse to make a pact with Gaia, and thus become Counter-Guardians?
Matou Sakura, for example, while pretty damn miserable in all but (IIRC) one of the ends, doesn't seem to stand up for herself enough to make such a pact, in most cases. She'd need to both get the idea, and have a reason that she thought was worth it. The only reasons that spring to mind right now, are needing power to save Shirou from something (and then only if she thought she could save him), or learning that Archer is Shirou, and deciding that the pact would be as close as she could get to being with him.
Its been suggested that Illya might make a pact to gain a longer life, perhaps by fixing the flaws in her body (thus also allowing her to grow up).
From Tsukihime, there are some fanon versions of Akiha who might make such a deal for larger breasts, but that's only appropriate for really silly fics.
Matou Sakura, for example, while pretty damn miserable in all but (IIRC) one of the ends, doesn't seem to stand up for herself enough to make such a pact, in most cases. She'd need to both get the idea, and have a reason that she thought was worth it. The only reasons that spring to mind right now, are needing power to save Shirou from something (and then only if she thought she could save him), or learning that Archer is Shirou, and deciding that the pact would be as close as she could get to being with him.
Its been suggested that Illya might make a pact to gain a longer life, perhaps by fixing the flaws in her body (thus also allowing her to grow up).
From Tsukihime, there are some fanon versions of Akiha who might make such a deal for larger breasts, but that's only appropriate for really silly fics.