Random Starting Point without Seek?

Question

I would like to achieve the following:

Event Start Playlist when entering a specific zone.

Playlist contains:
Track A
Track B

I want Track B to have a random starting point, similar to the Seek function. Track B should repeat until Event Stop Playlist.

So my question is, is there a way to have a random starting point to a track (or segment) somewhere baked into this without using more Events AND make that Seek have a Fade In, without needing to create more events?

But if I need more Events to achieve this, how can I set this up? How to let Wwise know to play Track B after Track A has ended and that Track B should have a random starting point (with a fade in).

Thanks.