Multiple copies of a survivor
So when joining a trial there can be, for example, multiple Dwights or Claudettes. I know this is probably not canon but maybe there is an explanation that makes it possible lore-wise.
We know that time in the Entity's realm doesn't work like in the real world. Maybe the concept of time in the Entity's realm makes a survivor exist multiple times in the realm and one of those copies is, for example, a Dwight that is experiencing his first trial (New player) and the other Dwight has been in a lot of trials and knows how to avoid the killer with efficiency (Veteran player).
This is probably a stupid idea but I want to know what do you all think.