Out of curiosity, I started wondering if keeping Jessa pregnant or impregnating her once she's finished her cycle would give you more money. For quick reference, you get $200 for impregnation and she will stay pregnant for a week (seven days). You get $25 to extend it by one day, and you can only do that once a day.
1. The impregnation method means that if you keep up on her cycle, every week on the same day in the morning or afternoon, you're guaranteed $200 a week. If there should be an all-day story event with one of the girls on that day, you could decide to extend Jessa's pregnancy the day before and get $25 out of it.
2. The continuous pregnancy method assumes that in order to get the next $200, you must bang Jessa again on the same day you impregnated her and every day after that for the next seven days. The problem is that you can't do anything on Sunday, so you miss out on that day's $25, and instead, it takes nine days to reach $200.
Also, again if there's an all-day story event, you'll miss another $25, and there's no way for you to make that back again because you're already banging her once a day. In addition to this, extending the pregnancy takes up a time slot: to keep that money flow up, you're going to have to go back every morning or afternoon and skip some other activity.