How often do you find yourself writing a fresh contract, for whatever purpose whatsoever (sandboxing, side project, work, etc.)?

More than weekly (but rarely ever deployed). Chisel has helped cut down on throwaway contracts a lot.

I go back and forth (between prototyping random ideas and actually fleshing one out), but during prototyping phase I'll sometimes write a contract just to see if I can model an idea properly on-chain. Hard to tell ahead of time.

Every day. It’s my job. Lots of tests and scripts, sometimes libraries or example/prototype contracts

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