@NathanAlvares24 Thank you for your help! Attached is a screenshot of the whole flow together. Ignore the breakpoint on line 7, I accidentally put it there before taking the screenshot.
Regarding the time format for "ClassTime", It has to end up as text, because it's going to be input into a text field using emulated typing, rather than an actual datetime field. It gets converted to datetime where necessary for math, but regardless, that particular variable value doesn't seem to be the issue, because like I said originally, the "While" loop runs enough times to create classes for each hour of that day, and it changes the class time each time, it just doesn't start back over for the next day.
Here are the variables before entering the loop for the first time:

I haven't been able to actually make it through the "While" loop again this time around because the "click link on web page" action keeps breaking and not being able to find the element by its ID, but that's a different issue. Because of that, I don't have the values of the variables after the first time through scheduling for a day.
Thanks again for your help