I like making clip playlists, for all sorts of content, and I have a LOT of them. But it finally occurred to me to try some of the other built-in features of iStripper. This may be because I am just slow at times, or because when I discovered playlists I never really looked back. However...
The built-in automatic card playing that iStripper does when it starts up is controllable enough that it can give really superior results. And you can get pretty much exactly what you are interested in, and with the right settings it will play ALL the content matching those parameters from each card before moving on to the next card. So each girl will be performing for a good while, not just the length of a clip. This, I have found, I like a lot.
The trick is setting Show Duration to "All clips" and then controlling the content with Levels of eroticism. I like setting both "Nudity and Full nudity" myself. That gives you a lot of variety in what clips are displayed.
And without any other changes it does this for each card in your collection. You just... let it run.