Hi Winn,
I'm really sorry that you're having trouble running OLS and GWR on your feature classes! In order to try to figure out what's going on, if you can provide the following information we can try to reproduce your problem and hopefully fix it!
-What version of ArcGIS are you using?
-What operating system are you using?
-What kind of feature classes are you using? Polygons, points, lines? How many features are there? Are they are in a personal geodatabase, a file geodatabase, or other?
-Does the problem seem data specific? For instance, if you try to run OLS or GWR on a completely different feature class, does it work? Or do all feature classes cause this failure?
If possible, if you could provide the dataset that was giving you trouble that would be very helpful in trying to reproduce. If this is possible, it will also be helpful to get screenshots of the tool dialogs before you run them, so that we know exactly the parameter choices you're making. If not, the above information should at least get us on the right track.
Again, I'm very sorry that you're having trouble, and we'll do our best to figure it out!
Lauren Rosenshein
Geoprocessing Product Engineer