Ok. So the "tokens" are RFID. You could indicate them as "schede", that means "cards". And "token" as "scheda" (1 card).
Pegs -> gancini
Peg -> gancino
Or maybe the first translation, "piolo" for peg and "pioli" for pegs. Let's wait for other opinions.
The #9 could be translated in different ways, but I think you should forget to use the same meaning that the original phrase as in your language. Every culture has its own common sayings 
You could use:
"Non so se di questi tempi ci si possa permettere di giudicare una persona dagli abiti che indossa"
Like the previous point, let's wait other opinions.