I can't remember the situation very well anymore but the sentence was like:
僕はお母さんに喜んであげる。
My Japanese boss corrected me quickly by saying "喜んでもらう".
So what is the difference between てもらう and てあげる? I am not sure about the sentence itself, but I know what I wanted to say in that situation: "I want to make my mother happy" (in a specific situation)
てもらう is something you ask someone to do for you. てあげる is something you do for them. I feel that てもらう is closest to "I'll have you V", as in "I had my sister cook dinner".
If you want someone to do an action, you want てほしい
I would say it sounds weirder from a contextual standpoint - that 喜ぶ is not a volitional action - you don't choose to enjoy or be happy, so the idea of doing that for someone sounds a bit off.
My teacher mentioned this may sound arrogant or imposing to use てあげる. For example: カレーを作ってあげます or 手伝ってあげます。 Is that the feeling you get from these examples too? Is it the tense that makes imposing? what if it was past tense?
Believe it or not, it simply depends on the person saying it and how they say it. It's not a very satisfying answer, but that's exactly what is said in the awesome grammar (paper) dictionary that I use. Basically, it said "if someone is not nice/friendly, it can come off as rude."
Although this is not clear cut, consider the two examples:
Someone is busy at work, and flustered. If you, in a friendly way, said "大変ですね、手伝ってあげようか？", it would come off as a friendly gesture to someone in need. However, if someone who thinks highly of themselves or lowly of the busy person and says more coolly "手伝ってあげるよ", it might sound like a "I will help you because you're incapable of doing it yourself."
