A: The order in which multiple columns should be transcribed may be predetermined by the restaurant's menu already. If not, then it should be transcribed left column first and then right column second.

In the example below, there is no obvious order to these two columns in the Appetizer category. They are not listed alphabetically and the items themselves are a mix of different kinds of foods (dumplings, rolls, wraps, fried seafood). 

As such, they should be transcribed left column first and then right column second.
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As you can see in the example below, these appetizers have been listed by the restaurant in alphabetical order. 

Therefore you should transcribe them left to right so that they remain in alphabetical order, instead of left column and then right column.

Another example:

As you can see above, the items on this menu are numbered and therefore should be transcribed in numerical order within their respective category.

Wine menus should always be transcribed left column first and then right column second.