i think he isn't smart either way. maybe because lack of experience since he is only level 2. if he wants to do like you said, as a seller he will get higher price but also lose some tokens for sure (in this case it's worse since the tokens lost will be multiplied by two). token can be converted to money and i don't think he will get any advantages of doing that
and more importantly, market value doesn't increase by a bidding war. market value of player still as is. that's why you should avoid unnecessary bidding war since that will get you pay extra cost for obtaining that player