1

I am not sure if the phrase "thing you can imagine X" can be used like I tend to used it in the past.

Here are some examples I thought of"

This is the last thing I can imagine doing.

This plane is the last thing I can imagine flying in the air.

The first one seems correct, because "doing" is attached to "I", but in the second one "flying" is attached to "plane", and this construction seems to be awkward and ungrammatical for that very reason. There's no apparent link between the two. Am I wrong?

2

The second sentence is actually ambiguous, but it's grammatical and understandable in both possible interpretations.

1. The normal interpretation is as follows:

This plane is the last thing I can imagine flying in the air.

Or:

The last thing I can imagine is this plane flying in the air.

In terms of actual meaning, it's saying:

I don't believe that this particular plane is airworthy.


2. But a less common interpretation, because it wouldn't make as much sense to most people, is:

This plane is the last thing I can imagine flying in the air.

Or:

The last thing I can imagine is flying this plane in the air.

In terms of meaning, it's saying:

I don't believe I could ever fly this plane.

Anybody who is actually a pilot might assume this interpretation before the other.

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