How do we split a two-words verb in a sentence if the object is a bit descriptive?

Let's see these two-word verbs first -

Wake up,
Kick off,
Pull out, and many more...

Now, I'm adding an object there...

Wake me up after an hour.
I'll kick him out.
You see a thread there? Pull it out.

A twist-

The above-mentioned examples sound okay (at least to me!) as the objects are just one word (me, you and it in these cases) but then when the object is descriptive, splitting of those two-words verbs appears weird. Check these now -

Go in the hall, and wake the person wearing shorts and a red tee up.
I'll kick that arrogant and annoying dull employee out.
Do you see many threads there? Pull the white, shining, powder coated warm wire out.

The question -

When the object is descriptive, should we keep those two-word verbs together? Say...

Go in the hall, and wake up the person wearing shorts and red tee.

And so on for the rest of examples?

If yes, is the sentence 'I'll kick him out' incorrect as it puts the object (him) between the two words of verb (kick & out) that otherwise come altogether (kick out)? But then again, I'll kick out him does not sound as good as I'll kick him out.

Answer

What governs placement of the particle is not the character of the object NP, but its weight—how long it is and how much stress it receives.

In phrasal verbs of this sort both the verbform and its associated particle must receive the same stress; this helps establish them as a single semantic unit. If the object of the verb is very ‘light’—one or two syllables, without prosodic stress—the object is placed between the verbform and the particle:

I woke him up.
I woke the man up.

If the object is slightly heavier—three or four syllables, with maybe one prosodic stress—the object may come either before or after the particle:

I woke some of them up. OR I woke up some of them.

But if the object gets any heavier than that it has to be placed after the particle.

I woke up the Captain of the King’s Guard. BUT NOT ^∗I woke the Captain of the King’s Guard up.

The important thing is to keep the verbform and the particle close enough together for the stress pattern to show that they are associated.

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^∗ marks an utterance as unacceptable.