[Cherry_Lover]

Originally Posted by RadiantBeam

And since I happen to not be horribly inclined towards Sakura/Shirou, I'd probably have a much harder time of it than you would, I admit. At the very most I'd probably end up developing a possible threesome situation, but then that would require forming a deeper bond between Saber and Sakura without sacrificing the feelings she already has for Shirou.

Well, I'd say that a threesome would be the absoulte least (or most, I suppose, depending on your viewpoint...) that Sakura could get out of such a situation without it going horribly wrong or you writing everyone to be miles OOC. The way HF develops is such that Shirou will inevitably fall for Sakura unless he pushes her away entirely, which results in her death and him becoming a heartless killer like his father (who would, therefore, see Saber as nothing more than a tool). Saber could wiggle her way in there too, if Sakura comes to care for her (which, if she's protecting Shirou when he's made it quite clear that his involvement is not conditional on having a servant, she might well come to do), but the Shirou x Sakura pairing is guarenteed to develop, because of how their relationship is set up and how HF goes. Shirou's feelings for Saber develop over the course of Fate whereas, in truth, all that happens in HF is that Shirou comes to realise that he's had feelings for Sakura all along, and just didn't see them until the events of HF happened, so it's hard to see a relationship with Saber developing whilst he's protecting Sakura, and if he doesn't protect Sakura HF doesn't work.

I've written characters I don't care much for several times and have pulled it off without complaints, so I'm rather certain that I could do it with Sakura if I wanted to.

Well, the thing with Sakura is that she's very open to alternate interpretations, and if you're doing a story like this (that necessarily needs to be sympathetic towards her), you kind of have to get her right, which isn't easy. It depends, fundamentally, whether you don't like her because you don't like how she really is, or whether you don't like her because you've misinterpreted her character (like a lot of people).

The problem is, IMO, I'm honestly not getting enough development on Sakura in-game at the moment to really feel like I grasp her character.

Well, most of her character development comes later on in the route, I think (depending on how far you've got).

Spoiler for HF:

Also, the fight with Rider would vary depending. As she's been depicted so far, Saber is extremely worn out from escaping the shadow and probably won't recover from it right away, so even if she wanted to fight Rider she'd have a difficult time of it currently in her condition. She has no real way of replacing the mana she lost from escaping, so she's very weak right now.

True, I suppose, although that likely wouldn't stop her trying. Of course, mana recovery through the 'standard' method is simply not plausible here (well, unless it involves a threesome with Sakura's consent...), so she'd have to either contract with Rin or Sakura or else lie there doing not much for the rest of the war.