Few items here:
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Weather holds should be tied to shipping strategy and not by state. That way if customers select a refrigerated shipping option or expedited service, the order will not apply a future ship date and piss the customer off because they paid for 2-day service only to have their order be held.
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Dashboard for orders at fulfillment over 5 days needs to include the shipping date so you can see why it is being held up.
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Override shipping date at time of order creation. Need the ability to enter a date and have the system accept it for shipping dates. If a customer approves the shipping date, and you enter it in, the system should not override back to the weather hold date.
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Viewing states on weather hold. The state profile screen under the Store section should indicate which states are on weather hold and have the associated date displayed.
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Managing weather hold orders should have a screen where you can see by state which orders are on weather hold and have the option to release them either in total or order by order. Please look at what you have at WineDirect for an example of how this should work.
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Customer self service weather hold release. If a customer wants to come on the site and release their order, there should be a simple checkbox approval for them to ship their wine.