Welcome to the ultimate test of bidding strategy.
Beware: The highest bidder often loses money. Can you beat the math?
Item value is between $0 and $100.
In an auction where the true value is unknown (e.g. 0 to 100), the expected true value of an item given that you win (i.e. your bid B >= true value V) is roughly B/2.
Even though you can sell it for a 50% premium (1.5 * V), your expected resale value is 1.5 * (B/2) = 0.75 * B.
So, on average, winning a bid of B earns you 0.75B. Your profit is 0.75B - B = -0.25B.
This is the Winner's Curse: winning the auction often means you overpaid!