Sounds like the first option would be the most interesting since it has the most branches and options off of it. With Izuku's interactions and the vague period, plus skipping the initial CR meeting can always be helpful later. And if he's gonna be comfortable and established, that'll help with Katsuki's later not-so-comfortable-and-established state.

While falling out of sleep and into battle would be fun, considering the attack will be pretty sudden and Izuku's going to try rescuing people Quirk or no Quirk, which means making even more quick CR, I'd say the second option is gonna be mostly covered for Izuku even if he goes with Alyce. Besides, he can still shout directions or warnings for Katsuki. Or toss him items and stuff. Depends on how much the "no violence" thing can be stretched.