Yeah, this is kind of exactly why Falling Stars is written as it is. You can do the first run with whoever you want to, you don't need to plan multiple playthroughs....choose who you like, be cool with her, or with THEM...that's it. Honestly, I'll probably include an option at the end to see all other possible endings because who has the fucking time? it's not like hordes of people are giving a shit about this game anyway, haha!I like this option as well, with a lot of long AVNs I often feel like you have to plan way into the future for choices you are making in the moment.
The only way you need to plan around is to be an absolute SHIT to get THE VERY BAD ENDING...but that's a thing you gonna have to consciously be playing for....and I certainly don't recommend it. You will NOT like it.