If I collected this club, or this kind of chip, I'd offer in the $300-500 range. If you are collecting for history, and not just for potential price appreciation, the damaged and drilled chips are still valid collectibles.

Incidently, I've never been completely convinced these old Flamingo chips without a dollar sign are really value chips and not roulettes. The design of the inlay on the smooth mold roulettes is exactly the same. Does the HCE mold make them value chips?