Oh if he was on the chart, I'd have chosen him. The only characters I've ever heavily identified with in Star Trek have been Stamets from being a hot mess, Hugh Culber for PTSD and O'Brien for 800 variations of Space PTSD.
then wake up and find out that you were in yet another prison simulation the whole time
You think maybe he'd wake up in the middle of the night on DS9, quietly whisper "Computer, end simulation", and then silently sob himself back to sleep?
If I had to pick in no particular order, I would be Lore, Q and Reg Barclay. With the later two due to the the first being literally impossible.
More like "retreat interactive VR power fantasies where you punch your boss and have sex with his girlfriend"
I'm a Data/Lore with a heavy dose of Q
Out of context that makes me look alt-right, I wish that douchbag had chosen X or something