For the investors family you need to get the investor to like you more. The number of scenes available depends on how much he likes you. As it goes up, there will be addtional opportuities to increase it. You don't have to let him molest you or your date to make progress, but it helps. There's a bunch of steps, and it takes around a year to complete. Longer if your club is not advanced enough and have to build the auxillary office. But as long as his opinion keeps growing you will be making progress. Also try to bring the same date each time. The she liking them and vice versa also helps.
And here's a hint: when someone you want to like you more birthday comes up, always send them the big gift. That adds a possibly overpowered +20 opinion modifier. Don't lose that opportunity when it comes up.
You can change the male probability via the in-game options. However, there's some benefit to having males in some roles. It doesn't matter for the PI but male commissioners are more likely to pass the stripper laws faster than straight females.
Ah. Yes, I was screwing that up. I hadn't gone for a relationship at that point, and when the events came up I was getting a random selection of women to choose from, and even the ones working for me were saying they were at work and couldn't get free. Later, when I did pick a girlfriend, she wasn't even always reliable. I am trying a girlfriend who works for the city this time, she should always be off during such events, we'll see how that works.
Also good to know, I was discounting the gifts in favor of calling because I at least got info some of the time, and I assumed that the complaint about wanting more meant it was always going to be a failure of some sort.
Started another game, and again, I have a male slut PI who is constantly hanging around my restroom, though he hasn't started wandering around nude. I'm going to see if I can convince him that casual sex is something he hates, along with public nudity, but so far I've been totally unable to convince him to change those opinions, and I suspect that at least some of the characters in non-club jobs have some interests locked.
I very much appreciate the responsiveness, it helps greatly.