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(i.e. if 80% of the time you don't do drop ship, that box probably need to be un-checked and vice versa) - at 50-70% probably a judgement call over what your staff would prefer to do (do they want to be forced to un-check it, or forced to check it, which causes less pain for the business if it gets forgotten at record save

Got it, thanks! And is there any difference on an accounting level (example - which accounts it will hit) if set on item or transaction level?

Drop ship is drop ship, whether you do it from the transaction or from the item

That said - drop ship GL impacts are different than special order GL impacts

With drop ship you get the GL impact at time of vendor bill

with regular inventory or special order - since you bring that inventory into stock, COGS occurs during item fulfillment