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Long answer; you can sleep with multiple girls in the beginning but later on you have to start making some choices which will result in you missing out on others.
In addition to this, there are quite a few secondarys in the game, and some decisions will mean you miss other scenes. I'd say no fewer than 15 playthroughs for seasons 1 and 2 would be needed, and even then, things just...change based on choices you make. Note that you can try for some of the girls and FAIL based on how you are playing the main character. Yep, you can get rejected.
Now I still need to figure out how to get the 4 missing 2D art thingies.