Hello, @Alvar007!
Thanks for taking time to update your new FLIRT animation. I did test it on my local install and I can show you what it looks like in this video here. Forgive the rather low resolution.
In the video above I set the FLIRT animation for the lines "Well, of course, darling. Whatever Tanis Venn can do. You know, very few human females come to Tatooine..." and "Sure you do. Tanis can tell you all about the thrill of the hunt, man versus beast. It's all very exciting."
As you can see there is a problem that I am also having with the drinking animation which is the cycling of the animation itself.
I don't know anything about how the game plays animations and how/when they reset them but ideally the FLIRT animation should always start with the winking so that if the dialogue line is short, there is still a good chance that the player sees it. For that reason it is also important that it is 2-3 seconds long. In the video the new animation you created doesn't almost ever start at the beginning but comes after some time. Many times the game doesn't even manage to play it because the spoken line ends.
Another problem is that it seems there is no actual winking (see from minute 1:16 to 1:21).
I have uploaded my files here.
Thanks again for all your hard work.
S_Male02.mdl S_Male02.mdx