Once I send a quote to the Lead, does the status automatically update to the next step, and once it gets to "Hold," do I need to send them the contract, or does it automatically get sent?
Everything will start in the "quote" status. It will not email the customer automatically anything unless you turn on one of the "Customer - Quote reminder" automatic emails. If you email the customer the contract, from the contract tab of the lead, it automatically updates the status to "contracted." Hold is only used to hold equipment for a lead before the event is even contracted (generally a temporary hold for a big lead on the hook that isn't ready yet to book, but you want to reserve some pieces for them).
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