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I’ve come across some adjective conjugation that I don’t fully understand in two separate but related example sentences, and so my translations are definitely wonky.

飲んでいるでしょう。その証拠に、ぜんぜんお腹が小さくならないじゃない.

Translation: Probably drinking? As evidenced, never stomach (something not little)….?

I know 小さくない means ‘not a little’ but this ならない is confusing me, I only know it from なければならない meaning 'must' but that' doesn't seem to apply here. The meaning overall is eluding me.

文法のルールが説明できるからと言って、それが上手に使えるとは限らない。その証拠に、実際に作文の宿題をチェックしたら、正しく書けていないことが少なくない。

Translation: Just because I’m able to explain the grammar rules doesn’t necessarily mean I’m good at using them. As shown, in reality when I check my homework essays I’m not able to correctly read not a little?

In this sentence, both the final verb and adjective are confusing me. 書けていない I think means ‘not being able to read’ whilst 少なくない means ‘not a little/not few’ but put them together and I’m lost.

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First, let us review the adjectives involved to make sure there is no confusion.

Size vs. Quantity/Frequency:

Size:

「[小]{ちい}さい」 = "small".

「[大]{おお}きい」 = "large"

Quantity/Frequency:

「[少]{すく}ない」 = "few", "a little", "not frequent"

「[多]{おお}い」 = "many", "much", "frequent"

Moving on to Grammar:

To express "to get or become (adjective)" in Japanese, you need to attach the verb 「なる」 to an adjective. In doing so, however, you need to conjugate the adjective into its [連用形]{れんようけい}(conjunctive form). Yes, just like verbs do, adjectives also conjugate in Japanese.

The 連用形 of 「小さ」 is 「小さ」. Likewise, 「少な」 to 「少な」.

「小さくなる」 = "to get small(er)", "to shrink in size", etc.

「少なくなる」 = "to lessen in quantity", "to become less frequent", etc.

連用形 is extremely important. If I, who is neither a teacher nor linguist, must use the word on a daily basis, that should tell you how important it is.

The plain negative form of an i-adjective is also formed with 連用形. 「小さ」 becomes「小さない」 and 「少な」 becomes 「少なない」. All humans live in the world of 連用形. In Japan, even animals live in the world of 連用形.

Finally, your sentences:

「[飲]{の}んでいるでしょう。その[証拠]{しょうこ}に、ぜんぜんお[腹]{なか}が[小]{ちい}さくならないじゃない。」

"You must have been drinking (alcohol). As evidence, your belly hasn't shrunk one bit!"

「その証拠に、[実際]{じっさい}に[作文]{さくぶん}の[宿題]{しゅくだい}をチェックしたら、[正]{ただ}しく[書]{か}けていないことが[少]{すく}なくない。」

I skipped the first sentence because your translation of that is good.

"As evidence, when I actually checked my composition homework, (I found that) there are quite a few things that have not been written correctly."

「正しく書けていない」 literally means "has/have not been written correctly". For a translation purpose, one could use "I have not written (or even 'did not write') correctly."

「少なくない」, which expresses high quantity/frequency, is one of those phrases that we native speakers use far more often than Japanese-learners do. It means 「多い」, which is what the learners tend to use.

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Adverb+なる means "to become", as in 学生{がくせい}になる (to become a student), 綺麗{きれい}になる (to become clean/pretty), or 大{おお}きくなる (to become big), so in the first sentence, 小{ちい}さくならない means "not to become small". In the second sentence, 少{すく}なくない is just the negative of 少{すく}ない, so it means "not a few" (i.e., many).

The first sentence is difficult to make sense of without context, but translated literally it could mean "(I/you/he/etc.) probably drinks (a lot/regularly). Doesn't that mean (my/your/his/etc.) stomach will remain large (not become small)?"

The second one is easier: 書{か}く means to write (not to read ;) ), so 書{か}けないこと means "things I can't write". So the sentence means "There are many things I can't write correctly."

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