Length data entry

I also clicked on the box somewhere that gave me an option to automatically fix issues

So you got into Preferences and clicked Reset Workspace which won’t have anything to do with the actual drawing or dimension entry. It resets the locations of some of the panels. And then you got into Model Info>Statistics and clicked on Fix Problems which fixes problem geometry but also doesn’t have any impact on dimension entry.

As long as it’s working, though…

It sounds like you would benefit from spending some time with the getting started videos from SketchUp Campus as well as the new training materials in SketchUp Campus

The fix issues button in the Model Info->Statistics panel checks the model’s geometry database for validity errors and tries to fix them. It has nothing to do with the operation of Tools.

Are you moving the mouse after you’ve entered the distance?

Yes! I have been watching YouTube university freverently lol. I’m not sure what fixed this issue exactly but everything seems to be working properly and easily now. Thanks for your help.