DMD is being developed much longer and it's pretty linear so the updates feel bigger.
You're missing the point. It's not about the size, it's about the consistent progress. Let's say relationship starts from 0 to 100. It doesn't matter if each update only adds by a tiny 1 point as long as it goes from 0 -> 1 ->2 -> 3 etc where each update showed progress. This is what I failed to see in Babysitter. There are updates where it didn't feel like the relationship progressed.
Passion route at the hotel might showed progress, but that's the latest update only. It doesn't really reflect the progress of each update. When compared to DMD, it is clear that each update progressed the relationship because the D increased her corruption level, and then it's actually consistently carried over to the next update (e.g.: she's comfortable being touched on this update, then she'll still be comfortable being touched next update, etc). That kind of consistency is what's lacking in Babysitter.
But point system could be improved even tho I have no idea how to do that now.
The easiest way to fix point system is to give clarity as to how many points are required for each choice. A simple greyed-out option for the ones we missed would make players realize that they missed something. Thus, having incentive to replay with different decision to reach that point requirement.
Example (player has 13 pts)
Option 1: bla bla bla (requires 10 pts)
Option 2: boo boo boo (requires 15 pts) -> greyed out and cannot be picked but it gives information what players need to do
Option 3: baa boo baa (no requirement)
The main reason why the current point system is bad is because players aren't being informed what they need. For example, if you have choices where it's Christine+1 or Jess+1, how do you know which one is more important down the line? We know there will be more Christine points than Jess' but we don't know how many points we need for Jess to unlock her content. So it's possible for players to go through the game missing a lot of content without realizing it, and it's awful idea to expect players to replay and go through again trying to make different decisions but still just as blindly as the first time because they didn't know what exactly needed to be different.