50? Then you're only half way done with the currently available girls. :D If you add Ash in the count, you can get exactly 100 girls pregnant in the newest update. And more will come in future updates.
The time skip will most likely happen on some sort of world map screen, where you can select icons to watch events that happen in that time periode, and then use a button to advance to the next step, wehre you can see more events. This way, the events that happen during the time skip are a bit spread out, to give them a feeling of time that has passed in between.
Not every child will receive a CG or unique character with story, but they'll most likely be a huge part of the content during and after the time skip.