"He considered whether to permit or not to permit."
Translation:Li konsideris, ĉu permesi, aŭ ne permesi.
I wouldn't say it's wrong, exactly, but it's not conventional. The extra "ĉu" isn't necessary. It's like saying "whether to permit or whether not to permit". It's not exactly wrong but most people don't add the second "whether" so it sounds a little strange. If you feel strongly about it being right, report it.
My instinct here was … aŭ permesi aŭ …
Someone tell me why that might be wrong.
That would be "He considered either permitting or not permitting". Which is a bit tautological, since regardless of what he does, it will be either permitting or not permitting - it has to be one or the other.
Or a bit more verbosely, something like "He considered the possibility of doing the following: either permitting or not permitting."
Your structure would make more sense in a sentence such as "Li konsideris aŭ danki aŭ plori sed finfine simple foriris" (He considered either thanking or crying but in the end simply left).
This is a sentence where you want to know the result of his choice: whether to do one or the other. Not just deliberating.
"Ĉu" is like "whether" here.
I think not - for me at least, rajtigi is more like "authorise": give someone the authority they need in order to do something.
For example, I might permesi my children to stay up late, but rajtigi someone to enter a restricted area.
Staying up late is usually not something you think of as involving authorisation.
Conversely, only people who have been rajtigitaj may check train tickets, but that's more about having the requisite authority than specifically about permission.
But if you "permesi" your children to stay up late, won't they say that they "rajtas" stay up? Or have I misunderstood the appropriate use of "rajtas" to begin with?
I would say that they are similar, but the nuance is different. "Rajtigi" seems more formal, and definitely a bit more active. You can permit your children to stay up late. You can allow them to stay up late. You can grant them the right to stay up late. You can give them permission to stay up late. You can grant them permission to stay up late. They all mean about the same thing, but I would never say they're exactly the same.