1) If you are an appropriately dressed woman, the bouncer at the gentlemans club will usually let you in. Until you get a club security sleeper, after which the sleeper will always let you in, but any bouncer other than the sleeper will never let you in. Consequently, for a woman it is much easier to get into the club without a sleeper than with one.
2) Gender and clothing handling here is probably not what it should probably be. As is, type of clothing is ignored, provided the quality is sufficient. If, for example, you are a man wearing a skimpy black dress, the guard will always let you in. This might possibly be appropriate during some stages of gender acceptance...but even so it is contrary to what I would expect. This club is a conservative haven. On the other hand, if you are a woman wearing that same dress, the guard may or may not choose to let you in. This is also contrary to what I would expect. In my own personal experience, it is much easier for any woman to get into clubs of this sort. Imagine the guard saying, "this establishment is for the enjoyment of men, only" To which the woman replies "Yes. And I'm here for the enjoyment of men, only, too." She will get in.
3) Whether or not the guard chooses to let you in, you do not immediately receive access to the "talk" option. However, if you move off the square and back, this option becomes available. I'm not sure what the intended handling was...but I'm fairly certain this wasn't it.
4) If the guard turns you down for any reason, it is possible to bypass him by attempting to force the door. This opens up the previously unavailable "talk" option, and as a result of the escalted security status from being watched while attempting to force the door will allowing you to "Bluff" your way out of the situation, and the guard will leave the area completely.
5) If you attempt this, but fail to bash down the door, and then spam "S - wait" eventually the conservatives will show up in force. However, they teleport to the inside of the establishment, and have some difficulty getting through the locked door. They will get through eventually, but you may have to hold down S for 20-30 seconds before they manage it. Which is odd, because presumably they would have needed to go through both you and the door to get in.
6) The guard is trivial to kidnap. It's pretty much completely safe to try as many times as you want, and it's consistently doable even with naked, unarmed founders with zero juice and zero martial arts skill on day one of gameplay. Give him some better martial arts skills and a gun or something.
7) If you succeed in seducing the guard, he leaves. If you then leave the square and return, a new guard has magically appeared in his place. If you fail to seduce him, you can step off and back as many times as you need until you eventually succeed in seducing him. The sequence down-up-t-b-space-space-repeat allows you to quickly and easily train up seduction skill as high as you want.
If you show up naked, it takes the guard entirely too long to decide to do anything about you, making this by far the fastest, easiest and most reliable source of stealth training. Which is odd, since he talks to you the moment you arrive, so obviously he knows you're there.
9) Similarly, showing up in appropriate attire makes him a trivial way to train disguise skill. Disguise skill should probably not be trainable multiple times on the same target. Standing in front of a target who has already identified you as "ok" should neither give further skill gains, nor require additional rolls to continually pass the check.
10) During "high security" the club guard is replaced by an "Enforcer." However, if your regular guard is a sleeper, then the enforcer will be a sleeper as well.