>>96470752
>But I'm frankly not confident that I could deal with all of the conceptual bullshit from Hercules, Cu, and Gilgamesh on my first Jump.
The Jump offers more than enough to deal with that. You mostly want high magecraft, mana reserves and Black Grail. That way you can pretty much deal with everything quite easily. Even Gilgamesh would be very hard pressed if you shallow the other Servants and also interface with the Grail.