should I translate должен with need, must, should or have to? Because it seems that in some questions it accepts different things
"Дóлжен" comes from "долг" - (in this case) "duty", another meaning is "debt". It can be translates as "must".
"Нýжно" comes from "нуждá" - "need", so it is better to translate this as "need".
"Should" is subjunctive mood, so it has to be translated due to this kind of mood, for example "слéдовало бы".
But all of these words, except subjunctive mood, are interchangeable in many cases.
"You have to wear my jacket" was incorrect, even though "to wear" is listed as an alternate choice for «надеть». Did I do something wrong?
"You must wear my jacket". I believe this answer should be accepted.. Agreement???
I think that надеть is kind of perfective aspect, you put something onto yourself and it is done, like in english if you put a jacket onto yourself you end some action you had started. The word одеваться however means to wear something which is imperfective (it has not ended yet and still continues)
Would "You should put on my jacket" work or is Должен generally stronger than that? If it is generally stronger, how would you say "should" (or a less strong form than must)
"Тебе следует..." is a less strong way to say it. "Ты должен..." comes from the root word долг, meaning debt (so, "you ought to..."). If you want to go even stronger, you could say "Ты обязан...".
That said, I feel like "you should" is often the best translation of "ты должен" in many contexts and should (ought to) be accepted here.
A less strong form will be "Тебе следует...".
Even less form will use the particle бы and the subjunctive: "Ты должен бы...", "Тебе следовало бы..."
The error reporting function does not allow comments, and there are too few choices. It is good though to note that others have noticed the inadequacy of the only accepted answer. The dictionary shows several translations of the word «Должен» which this program should accept, including 'must' and 'should'.
It may be due to the fact that "надеть + что-то" (to put on sth) and "оде́ть + кого-то" (to dress [up] sb) do mean differently. Just like in English, in some cases, "to put on" is used, while in other cases, we have to use "to wear". Although I have to say that "to wear" also sounds well and suitable for the translation~ (so I've reported)
This does not convey the correct meaning. 'To dress a jacket' would me to gussy it up.