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My question is basically this one, except the Illustrator version.

I can think of some hackish ways to do it, but I'm thinking maybe there's a proper way to do it, so I figured I'd ask.

Chapter 1
1-1. The table of contents should have dotted lines like this..................4.
1-2. Ideally the dotted lines will resize with the text........................8.
    ◇ Some subset of 1-2 where there are no dotted lines
    ◇ Another subset of 1-2
1-3. And we're back to dotted lines again.....................................16.

Yes, I realize most people will use InDesign for this sort of thing. But it's not on the scale of a "publication"; just an informational PDF. And Illustrator is what I've got to work with.

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You do it pretty much the exact same way in Illustrator as one would in InDesign.

Lines should be formatted as: Text Tab PG#.
It can often be helpful to add a space on either side of the tab, but that's not mandatory.

Select the text and then choose Window > Type > Tabs or
hit Ctrl/Command+Shift+T to bring up the Tabs panel.

On the Tabs Panel, insert a right-aligned tab after the page number by clicking the area above the little ruler and be certain the right align option on the panel is selected.
(Any of the tab alignment options will work — depends upon the desired alignment of the page numbers.)

Then insert a period (or any other character) into the Leader field on the panel...

enter image description here

It's also possible to add a period then a space or two, just using the spacebar, to the Leader field to create some distance between the dots. There is a character limit to the Leader field. But, I don't recall what it is exactly. The image above is just the period as a leader, the image below has a period followed by a few spaces for a leader.

enter image description here

Illustrator has no TOC generation functionality like InDesign.
You'll have to manually build any TOC yourself.

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