I never lived in a communist country, so I am not qualified to give an answer. However 1986 I went with my family to DDR for a summer vacation, so I hope I can narrate my experience as an answer.
I know it's strange, but my father was organising the export of used medical equipment as a development aid. That's why we also went to Cuba 2001. People, especially working at hospitals, were very friendly to us in both countries.
I was 16 years old and an avid consumer of the local library. I used to borrow half a dozen books at a time so I can read during the long journeys. This time however was different. My mother censored my selection of books. I was not allowed to take Karl May books, for example. She told me that at the border to Germany we will be searched thoroughly. My father will throw away any newspapers a few kilometers from the border.
I realized that DDR is different and got a strange sinking feeling in my stomach. At the same time I was excited.
The border was in the Thuringian forest. The highway was one of the old ones from before the war looking similar to this picture: neglected and almost empty.
