Is it possible to use check boxes with value lists to input into a repeating field? Right now I seem to be just adding more text to the first repetition.

Yes, but the field would have to be formatted to display the extra repetitions. If you select an item in the first repetition, it will be added to that repetition. If you select an item in the second repetition, it will be added to that repetition, etc.

So it sounds like I'd have to have the value list & check boxes displayed multiple times. Is there any way to avoid this?

You can have the selections made on a non-repeating field and then use a repeating calculation to extract each selection. But would you need them in a particular order? What is your purpose exactly?

I'm doing workshop selections for a conference. I'm using a repeating field because eventually I want to generate tickets that will print on a sheet that the attendees pick-up, which also includes their nametag.

I don't need the selections in any particular order, however it would be nice to have them sorted chronologically.

I'm using IWP, which I know is very limited, but I don't have the time to teach myself custom web publishing. (I promise I will eventually, but I gotta get this project done first...) I know that one limitation of IWP is that checkboxes and radio buttons don't line up nicely. However I found a workaround by creating a separate value list for each selection and displaying the field multiple times, each time with a different one-item value list. But now I hit a wall with the repeating fields.

What exactly do you mean by a repeating calculation?

Okay, then you can create a calculation field of

Substitute( MiddleValues( Extend(options); Get(CalculationRepetitionNumber); 1 );