Prepositional Phrases of the Young Writer of the Blog

From the wise words of a starfish.
Created completely with MS Paint. Really.
And yes, you did see this on Twitter.
This is more of a quirky grammar convection than anything, but have you ever written a phrase where you have a prepositional phrase (of a prepositional phrase [in a sentence])?

There, I just provided an example. I'm not sure if it's grammarly correct, but I stumbled (over this) when I was going (over prepositional phrases) (in Comm Arts). Technically speaking, a prepositional phrase isn't a core part (of a sentence). However, this brought (to my attention) grouped prepositional phrases (of a wordy nature)(in my writing).

Okay, I hammered down that point. I'm not saying not to use prepositional phrases, considering how many I used it that last sentence, It's nice to know that there are a lot of them, therefore leading to many cases were they can go wrong.

A  Few Examples:

While in some cases it isn't that bad, I caught myself typing this out in a forum thread (parentheses added):
Personally, The Hunger Games affected the level (of maturity/violence [of YA]) (as a whole), by taking some of Harry Potter's streak of darkness.
Try parsing that. For example, how would the sentence change if I chop one of them off, or rearrange them? And isn't the use of double "of" a bit awkward? That was the mistake I found myself making the most.

I could have rearranged it as this:
As a whole, The Hunger Games affected YA's maturity and level of violence by taking some of Harry Potter's streak of darkness.
Different flow, but less words. Would you say it's better?

But when you have examples like this:
Finn had been sneaking (out of the house)(in the middle [of the night]).”
While it looks clunky, "in the middle of the night" is a natural phrase. Oh, and in this case, it's not tripled nested. You can take out "out of the house" or "in the middle of the night" without wrecking the structure or even change the meaning. If you take out "in the middle" or "of the night", flow goes out of the window. Consider that.

It's a case-by-case basis. Really, flow matters.'

YOUR TURN: How many times had you ever used a prepositional phrase within a prepositional phrase that turned out to be awkward?