In reality, the most challenging aspect of SSB is the use of non-standard terminology. For example, I often have to represent the letter "G" with the callsign for Germany, and similarly, the letter "I" is represented by Italy, and "M" is replaced with "Mask," and so on. Numbers are even more interesting; some people find that the number "4" sounds ambiguous and therefore use "three plus one" instead.
This is very difficult to master through simulation alone. There are also other issues such as background noise and static electricity.