Honestly if I were you I'd probably just save my money.
If you are set on rolling though just go with what has the lowest chance to disappoint you, so rider.
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So like apparently everyone else, I'm stuck between Rider and Caster, with the possible throw in of Assassin, but I'm not looking at that too seriously.
Here are the stakes:
I want Waver from the Casters, but I already have a Tama, and I don't particularly want Sanzang.
I want Ozy from Riders, and would be happy with Drake, but I don't particularly like Medb or Quetz personality wise.
Assuming I don't get him, I will be rolling for Ozy at Valentines, and failing that, Boys Collection. I'll be doing this even if I get a different rider, because Ozy is cool, and he works well with Cleo, who is the servant I currently have the most fun with.
Waver is also in Valentines and Boys Collection, so if I get Ozy, any excess SQ can go towards him.
So basically, a 33% chance of a good roll in Casters, or 25% chance of a good roll in Riders, with a 50% chance of an ok or better roll.
Honestly if I were you I'd probably just save my money.
If you are set on rolling though just go with what has the lowest chance to disappoint you, so rider.