Actually, I haven't felt that experience in my last game.

Out of all my sailing trips with a Karve and longboat, I think only one ended up with having the wind blowing against me. And even that one changed pretty fast to a better angle not long after I had begun tacking. So even that was done by two turns before being able to sail straight again.

However, I think the biggest problem isn't the wind, but more that players think they will immediately loose velocity the moment the wind is shifting from their back to one of the sides, or even partially in front of them.
As long as the wind symbol remains white, you can sail ahead. Even if it means you need to turn your boat a bit.

Thorin :)