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Here are some example sentences:

We should replace all round steering wheels with a steering wheel that's rectangular so we are more alert when driving.

We should replace all round steering wheels with steering wheels that's rectangular so we are more alert when driving.

I keep forgetting if it's ok to use a singular in sentences where the object is plural and with the preposition with. I think it's wrong, but I think I saw many occurrences where it's used. I think it's wrong, because it makes the sentences very ambiguous.

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Yes, there is a choice. But your second sentence, given that it uses the plural, is ungrammatical.

It should be:

We should replace all round steering wheels with steering wheels that are rectangular so we are more alert when driving.


Nobody would think that if you use the singular you mean that you should replace the millions of existing steering wheels with a single steering wheel. That wouldn't make any sense. There is a degree of translation that goes on in our heads when we see the first sentence. There is nothing actually ungrammatical about it, and it's also something that's used idiomatically.

Note that it's possible to rephrase the first sentence so that all parts of it are explicitly singular:

We should replace every round steering wheel with a steering wheel that's rectangular so we are more alert when driving.

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