その上(うえ)Besides, In addition, Furthermore

なお② and その上 are both formal expressions used at the start of a sentence to add information. They can overlap in meaning, but その上 often implies that the following point is notable, while なお② simply adds on. Additionally, requests or instructions can follow なお②, but usually do not follow その上.

それに and その上 both add information. それに is neutral and casual. その上 has a slightly more formal tone and implies building upon the previous statement, e.g. 彼は優秀だ。その上、性格もいい ('He's capable, and what's more, he's kind too.').

その上 and 上に both convey the idea of in addition, but differ in structure and tone. その上 is a conjunctive adverb used between sentences, as in 彼は遅刻した。その上、宿題も忘れた (He was late. On top of that, he forgot his homework). 上に functions within a sentence to link clauses, and is often used in more structured or descriptive contexts.

その上 and おまけに both introduce additional information, but differ in nuance. その上 is neutral and simply adds or emphasizes information. おまけに often conveys a negative situation or unexpected outcome, sometimes with a nuance of irritation or frustration, as in 雨だった。おまけに風も強かった (It was raining. On top of that, the wind was strong).

その上 and しかも can both appear at the beginning of a sentence to introduce additional information. They are often interchangeable, but しかも is somewhat more colloquial and can imply that the added information is unexpected. その上 is more neutral and formal, with no such implication.

その上 and 更に are both relatively formal expressions used at the beginning of a sentence to add information. While often interchangeable, they differ subtly: 更に can imply that the added point is of the same type as what came before, while その上 can highlight that the following point is particularly notable or worthy of emphasis.