Interesting topic. I think there is a pretty wide variety out there. I do not think you'll have to try everything to get an idea.
The surf description of tails only holds to the extent that you get an idea. Tail respond different in kiting because we normally ride faster. I think there are more than two tail types because they have categorically different advantages, but I understand where that idea is coming from. I definitely think LC is onto something when being critical to shapers...but I do not think the tail shape is where they should be more critiziced...but thats another story.
This gives an indication:
https://barefootsurftravel.com/livemore ... ail-shapes
I tend to like pin tails on guns, and squash / bat tails on my powered board, and wide tails like a fish-ish or wide square on my trick / lightwind / smaller wave board.
One think you'll notice is that wide square tails will loose control at speed. They flatten out and becomes much harder to control, therefore a fish tail is an advantage if you go relatively hard at a wave with a light wind board. A fish tail is more complex to construct and gets damaged easier.
Pin tails keep in control, but will usually come on gunny shapes that do not turn as fast.
The squash / bat tails keeps boards a little wider towards the back, but still some taper to keep in control at speed. I tend to like to ride powered and hit the wave, therefore this is my overall favorite.