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I asked this Q in ELL, but I found related Qs here.

Here is a numbered run-in list sentence.

(A) The UI program provides temporary income support to (1) eligible unemployed workers while they actively seek new employment or obtain vocational training ; and to (2) those who take time off from work due to sickness, pregnancy, childbirth, or to provide care to a critically ill child or a sick family member with a significant risk of death.

Without the numbers, it would read:

(B) The UI program provides temporary income support to eligible unemployed workers while they actively seek new employment or obtain vocational training and to those who take time off from work due to sickness, pregnancy, childbirth, or to provide care to a critically ill child or a sick family member with a significant risk of death.

Here is my problem.

(1) Usually, in a two word/phrase list a comma is not used before "and". Also, my sentences are not both independent clauses, hence the conjunction should not have a comma before it.

(2) In a run-in list, if there is internal commas, then the items should be separated by semicolons. My clause (2) has internal commas.

Now, these two guidelines conflict in my case. All examples in the Chicago MS contain 3 items or more.

I have seen all these Qs asked here before. 1, 2, 3. What I gathered from them is that in a special case when a two item sentence is complex, there can be a comma before the conjunction. But I am still confused as to what it should be when it is a numbered list.

My questions is, in the case where there are two items (and those items have internal commas) is it still the rule to put in a semicolon before "and"?

In my view, 'Guidelines' are just that: guidelines; they are not rules that must be followed. Does the additional punctuation make it easier and/or clearer for the reader? Does it save the reader having to do a 'double think' and/or having to go back and re-read the sentence? Unless you are writing for a publisher who has strict rules about such issues, then do what seems appropriate and what you think would be clearest for your readers.

Personally, I would put a semicolon after "training" in both forms of your sentence. In fact, I would go so far as to say that it is more important in format B than in format A, because format A already has the numbering that clearly separates the two groups, whereas B does not have that extra 'break'.

For similar reasons, I would argue that the use of a semicolon (as opposed to a comma) is more important in B than in A, because again the numbering in A makes the division of the two groups clear. On the other hand, B already uses commas within the second section, so it needs a stronger indicator than a comma (i.e. a semicolon) to separate the two main groupings.

Clarity to your readers is more important than arbitrary rules!

P.S. I'm writing this as a Brit, not an American, so the opinions on your side of 'the pond' may be different!