Well. The game is designed in a way that you get a lot of girls at the same time, so of course I'm trying to level them all at the same time. That's what the game is designed for you to do.
I'm going to disagree here, as I'm one to argue that the game is designed to be replayed. It just allows you to chase multiple women, granting you less wiggle room for each additional one. While you may see that as bad design, you might be looking at it through the lens of a game where you're supposed to get everything in one run.
Oh, sure, this is rich coming from the nut who is Meta-ing the bejeezus out of their current run. But allow me to take a moment to explain my earlier reasoning for the "DON'T UNLOCK CASSIDY" rule of an Emma playthrough, as it will get my point across:
Am I suggesting to delay unlocking Cassidy because she hard-locks you out of Emma's content? No, because the actual correct move for an Emma run is to tell Cassidy to pack her bags and kick her out of the game. How so? Because keeping Cassidy around as a pet is a move that makes MC Mike the type of guy that Emma is not a fan of, as the shift in tone that going from lowly code monkey to entering a dick measuring contest against Dwayne (with enough murder, intrigue, and a power struggle that draw parallels to 1982's
Conan the Barbarian*) would suggest.
Mechanically speaking, it makes sense for Cassidy to interfere in Emma's route, as it fits their characters. Plus this is how I get the impression that the game is designed from a replay mindset, because their are multiple playstyles available. It just so happens that Emma's route works best with a "Don't be a Horndog" method of play.
Don't get me wrong, I'm not saying this game is perfect as it is right now. Personally I think a new game could start off a bit quicker (particularly NG+ starts), and in general a playthrough's length feels way too long to properly motivate triggering an end scene & starting over again. How to do that while not butchering the current sandbox mechanics? Hell if I know, so I'll be quiet & content with what's on offer for now as it's still pretty good, if a bit rough around the edges.
Back to my point though, this game isn't one to be played from a "Gotta
catch bang 'em all!" mentality. Instead I suggest to take your time, get your nose out of the wiki and pay attention to each girl's route individually. If you can do it that way, you might see that those surprise dead ends are a little more obvious than you would think, plus you're likely to enjoy the game a lot more.
[*Don't try to tell me that the phrase "Crush your enemies, see them driven before you, and hear the lamentations of their women" does not fit perfectly in that storyline.]