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As titled, I have difficulty telling when to use "致します" or "申し上げます" as opposed to the other one. For example,

ご連絡くださいますようお願い致します/お願い申し上げます。

ご愛顧を賜わりますようお願い致します/お願い申し上げます。

here is another one

お待たせを申し上げまして、大変に失礼をいたしました.

お待たせをいたしまして、大変に失礼を申し上げました。

  • That's a great question! I myself am also still trying to navigate the perilous and complex world of Japanese words for politeness. As far as I know, 申し上げます is clearly more polite than 致します. However, there is also such a thing as too polite, so it's kind of up to you to judge when it's appropriate to use 申し上げます and when it's more appropriate to use something less polite. For example, when I'm sending emails to professors, I will probably use 「お願い申し上げます。」 However, when I am emailing the undergraduate students I supervise, I will use either 「お願い致します」or「お願いします」 depending on how close we are. – Halfway Dillitante Apr 26 '18 at 7:58
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    Related: japanese.stackexchange.com/a/28597/9831 – Chocolate Apr 27 '18 at 5:12
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申し上げる is the 謙譲語 form of 言う (say/state). お礼を言う、お願いを言う。It is also used in the sense of ‘to do something’ (in a positive way) for someone who is respected or above the speaker in station.

致す is the 謙譲語 form of する (do). お待たせする、失礼する。

These are different words, albeit with occasional similarities and overlap in use and in nuance.

In many cases, 申し上げる is an even more polite form of 致す.

The main difference would be that using 申し上げる implies that you are doing/have done/will do something positive, whereas 致す is more neutral and can be used for expressions showing both positive and negative actions.

If you think of it this way, your example: お待たせを申し上げまして doesn't make sense, as making someone wait is not a good thing.

お待たせを申し上げまして、大変に失礼をいたしました。

お待たせをいたしまして、大変に失礼を申し上げました。

These sentences are not the best examples.

First, using the particle に after 大変 is, in this case, not grammatically correct. In this usage, it is a nominal adjective. In the expression 大変になる, on the other hand, 大変 is functioning as a noun with a different meaning and conjugation.

Second, お待たせいたしまして (make someone wait) is the set expression. お待たせ申し上げまして ('make you wait') is stating something regrettable (negative) that was done and is not used.

Third, I assume that you are aiming for an apologetic expression. お待たせする and 失礼する are both explaining what was done to necessitate an apology. They are the lead-ins. 'I was rude for making you wait' is not a valid apology and this combination would not be used in Japanese. Either 'Sorry for being rude' or 'Sorry for keeping you waiting' are more appropriate, as shown in the examples below.

お待たせいたしまして、お詫び申し上げます。

お待たせいたしまして、申し訳ございませんでした。

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    申し上げる is the 謙譲語 form of 言う (say/state). お礼を言う、お願いを言う。... Simplify 申し上げる to 言う <-- But... 国語辞典 says "申し上げる 🈔〘補動〙《「お[ご・御]…申し上げる」の形で、間に動詞連用形や漢語サ変動詞語幹が入って》謙譲 Aに~ する 、Aを~ するという動詞について 、Aを高める。「先生には私からお届け申し上げます 」「謹んでご案内申し上げます 」「いずれ改めてご相談申し上げます 」... 「お[ご]~する」より敬意の度合いが高く…" <-- These don't mean 届け(を)言う、案内(を)言う、相談(を)言う, but are the humble language of 届ける、案内する、相談する, right? – Chocolate Apr 26 '18 at 13:38
  • tl;dr's usually go at the beginning... – istrasci Apr 26 '18 at 14:47
  • @chocolate From what I have observed and read, when 申し上げる follows 案内 or 届ける it is in reference to a verbal communication (spoken or written), in other words to 'give verbal instructions' (案内) or 'report verbally' (届ける). When physically guiding someone or physically delivering a package I believe 致す would be more apt. I have read in a couple places about regarding 申し上げる as a humble/polite form of 言う. This is not my invention, but it does mesh with my overall conception of the usage. I do hope that I'm not mistaken. – BJCUAI Apr 26 '18 at 20:15
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    'give verbal instructions' (案内) or 'report verbally' (届ける). -- Nope.. When physically guiding someone or physically delivering a package I believe 致す would be more apt -- Nope.. You'd use 「お/ご~申し上げる」 in these contexts, too. 「お/ご~申し上げる」 is an even politer form of 「お/ご~致す」. regarding 申し上げる as a humble/polite form of 言う -- Correct, but note that 申し上げる has two meanings/usages : 🈩 humble form of 言う, 🈔 (used in the form お/ご~申し上げる) humble/politer form of お/ご~する. – Chocolate Apr 26 '18 at 23:27
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    あーたこの質問者と同じ状態→ detail.chiebukuro.yahoo.co.jp/qa/question_detail/q1366995953 ググったら説明がたくさん見つかります、例えば tap-biz.jp/tap_cat_100401/tap_cat_100405/1001034 謙譲度が低い順に「送ります」→「お送りします」→「お送りいたします」→「お送り申し上げます」 ... あと「お慕い申し上げます」「お察し申し上げます」とかもあるよ – Chocolate Apr 26 '18 at 23:38

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