I have encountered people using double negatives before. After I told my exchange students I was 可愛くない, they insisted I was 可愛くなくない, and we just kept on adding more くないs from there. However, I’m not sure if that structure is natural in normal conversation.
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That’s so かわいくなくなくなくない that it makes me want to cry
hehee
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The exchange students seemed to think so too…
But it was 可愛くなくなくなくなくない！
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いいえ、可愛くなくなく泣く泣く 
です
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Finding it was harder than I expected, but I was sure Dogen had a video about it.
Of course 面白くないわけじゃなくない？ was an exaggeration made just for the joke, but I’m sure I’ve heard Japanese people saying the following:
なくはない
ないわけではない
なくない？
The question one is specially tricky because it effectively reverses everything again. And if you happen to be using an adjective that has ない by default such as 少ない or きたない, things get out of control.
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After reading this whole topic I don’t feel confident in my Japanese-verb-construction abilities anymore. As others have pointed out you can’t attach させる to させる but you can attach られる and させる and vice versa. And that’s probably the form that @Leebo is trying to find: 食べさせられる. This literally means “Someone is forced to eat”, beware that られる in this case is the passive conjugation rather than the potential form (both use られる).
Double negations in Japanese are pretty difficult to understand, especially when you associate them with particles and state-of-being. Let’s take @SyncroPC examples:
面白い (interesting)
面白く (with interest, this form isn’t really used alone but it is useful to create other forms)
面白くない ((it’s) not interesting)
面白くなく (without interest, again you can’t really use this alone)
面白くなくない ((it’s) not without interest).
Now let’s take 面白くないわけではない: it literally means “It’s not like (わけではない) it’s not interesting (面白くない)”. Notice how it becomes sensibly easier when you break down the phrase.
Now let’s take 面白くないわけじゃなくない. This is by far the most difficult one among the others, and I’ve rarely heard it used in practice.
We know 面白くない means “(It’s) not interesting” and we know “わけではない” means “It’s not like”. This time the phrase is slightly more casual: わけじゃない is just the casual form of わけではない. So what happens when you negate わけじゃない? It becomes わけじゃなくない which roughly translates as (I’m not entirely sure on this one) “It’s not like it’s not”, also notice this affirmation is implicitly asking something (Japanese people love asking question without か and just using ない, so we can safely assume this is one of those cases).
Now let’s rephrase “It’s not like it’s not (わけじゃなくない) (it’s) not interesting (面白くない) (?)”. Since there are two negations this might sound complicate, think of it as they are “merging”.
The phrase then becomes “It isn’t like “it is not interesting”, is it?”, that is my closest interpretation.
Notice that an almost identical concept can be conveyed using: “面白くないわけじゃないか”. In this case the translation should be: “It is not like it is not interesting, is it?”, although I actually wrote the same thing they sound different within my head. In the first phrase the person speaking is actually seeking a confirmation that it is not “not interesting”, he is also seeking this confirmation in a somewhat detached way, as if he wasn’t involved (but he is). In the second phrase, the person speaking is straightly asking for a confirmation whether (it) is not interesting and suggests that he thinks that is the case.
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I remember some source saying that you always go to causative first, and then passive, and never the other way around (～させられる rather than ～られさせる). Couldn’t tell you for sure if that’s a rigid rule that makes grammar implode completely if you break it, or just something else that’s more confusing than it’s worth, though.
Well, “I’m forcing someone to force someone else to eat” (double causative) isn’t the same thing as “Someone is being forced to eat” (causative-passive).
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Couldn’t tell you for sure if that’s a rigid rule that makes grammar implode completely if you break it
You will never see a 食べられさせる when られる is passive, so that’s right, you can’t flip it.
But don’t be confused if you saw 食べられさせる, here 食べられる is actually the potential form (although in practice, I’m not sure if it’s common, but grammatically it’s correct) (Actually I’m not so sure about this point)
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I’ve no idea if it’s natural Japanese, but in my head I can see something like this making sense, with the ようにさせる construct that @Leebo pointed out as a possibility:
部下がSNSで機密を漏らしたので、良い社員にもかかわらず、俺は社長に辞めさせるようにさせられた。
Because one of my people leaked classified information onto social media, I was forced by the company president to let him go even though he was a good employee.
No, we weren’t discussing the causative passive. The nested causatives are what we wanted and ように is the best way to do that. Causative passive is something else.
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No one brought up or used the passive…?
Sorry I can’t read and thought you were replying to me not someone else. Trying to get the hang of this forum thing still 
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Of course you can use circumlocution, since you mentioned “other kind of construction” I assumed you were searching for a tense 
. @NLeseul that’s the closest you can get with ONE verb alone, if you use it alongside subject and topic you can get pretty close to the original meaning. As mentioned above, I believe the ように way will do the trick, but I also think there should be an easier way to convey the same thought.
You actually can stack up the させる, it’s just confusing and unnatural. If you add passive, you’re completely changing the meaning. Which, you could do if you find a way to structure the rest of the sentence to make that work, but we were kind of just trying to test what can be done with causative.
Can you? I’ve never heard of stacking させる, nor have I ever seen a rule about it…
Here’s a stack exchange question and answer, where a native speaker explains that it’s possible but confusing. In any case, it’s not recommended to use it.
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That person’s third (gibberish) example sentence with a triple causative appears to end up with three different nouns marked as targets of a causation with に. I’m suspecting that that’s the main reason it’s not really recommended; you run out of ways to keep track of which target is associated with which instance of させる really quickly. Adjectival clauses keep the sentence generally better organized.
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