English translation doesn't make sense

Question

In the lesson, these sentences do not make sense to me in English:

Ofrecerían más descuentos cuando pasara la temporada de invierno.They might offer more discounts when the winter season was over.Pararíamos para descansar cuando llegáramos a Toledo.We might stop for a rest when we arrived in Toledo.
Why are pasara and llegáramos translated in English as the past tense when they refer to future events that haven't happened yet? It sounds more natural to me to say "when the winter season IS over" and "when we ARRIVE in Toledo."

Answer

I also find the translation a little confusing, but that's because I read it as being in the past, or habitual, as in the example of reported speech.

"They used to offer more discounts when the winter season ended."

"We used to stop to rest whenever we arrived in Toledo."

But the way the lesson explains it, that would be an incorrect understanding. It's more tentative. They're not so much future events as unlikely events.

For the first sentence, "Yo te ayudaría cuando tú empezaras a comportarte bien.", I would translate it as "I would help you if you ever behaved yourself."