One situation in which you can do so is after time-related prepositions, such as in your sentence. Other examples in involving time-related prepositions: “After I ate dinner I went to sleep.” = “After eating dinner I went to sleep”. “Before you cross the street, look both directions” = “Before crossing the street, look both directions.”

The expression "to have problems/issues/difficulties/trouble + -ing" has a fixed form. You have to learn it specifically. When you come across other fixed expressions with gerunds or infinitives, you need to learn them individually too. You won't be able to find consistent rules in order to minimise your work but over time, you will develop a sense of what "feels" right in different circumstances. This will help you to guess in doubtful situations.