re: 300 lbs of crawfish for party - Buy them boiled or boil ourselves?

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I'd hire someone with a big catering rig to come do it

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This. My wife used to be in charge of corporate events for 50-75 people. We tried all three... boil ourselves, buy boiled, and cater. Cater was by far the best. Only problem is weddings, birthdays, etc book caterers up quick.

BTW you can suppliment with cheaper shrimp and crabs. Cooking for a number of people is half the $$$ when using shrimp.