大抵当初の思惑通りに事は運ばないッス。
The man looked upset because the result was different from what he had expected originally.
The man seemed disappointed because the result didn't live up to his expectation.
The young lady was wondering whether she should apply for the workshop.
The elderly woman was surprised to find that her favorite store was closed down.
upsetの他に、puzzled, embarrassed, resentfulなどが使えると思うッス。
その後、Q&Aの1問目で、If you were in the same situation, what would you do?
と聞かれるッス。
２．については
＜時間・原因＞
After that / Afterward
Through this experience
Because he had made a terrible mistake (in 〜),
As she had been involved in a similar incident before,
＜結果＞
He decided to change his way of thinking.
He had made up his mind to save the old building.
She was thinking whether her remark was suitable to the situation or not.
She applied for the workshop and then was looking forward to participating in the seminar.
