My guess would be that there are times included with your dates that are tripping things up.

For example, let’s say “Now” is December 15th at 3pm.
Therefore, tomorrow (Now + 1) will be December 16th at 3pm.
If your Start Date is December 16th at 4pm, then it will return false.

In this case, you might be better to first convert all your dates to integers. That will eliminate the time as a factor.

So, to get today, use the following:

Year(Now) * 10000
+ Month(Now) * 100
+ Day(Now)

Tomorrow will just be the above, plus 1.

So that will give you:

Today: 20221215

Tomorrow: 20221216

Then use the same math formula on your dates, and change the if-then-else to do a numerical comparison: