I'll offer a perspective: Python is in more widespread use in the geospatial arena. It is the scripting language of choice for ArcGIS and QGIS and there are a wide variety of high quality libraries available for it, plus community.
Python/Django/GeoDjango are a mature combination, with a somewhat slower, steadier development pace than Ruby/Rails/RGeo, which may be a pro or a con for you. Arguably, the GeoDjango documentation is better than RGeo's.
Ultimately I believe it comes down to developer preference, experience and productivity. If you look at the work of Vizzuality (github), they do some spectacular stuff with the Ruby stack. I'm not aware of any GeoDjango shop with such an impressive portfolio, but please post here if anyone knows of one!
This post by Jeff Atwood on why he chose Ruby to build Discourse is salient:
But why Ruby? Well, the short and not very glamorous answer is that I
had narrowed it down to either Python or Ruby, and my original
co-founder Robin Ward has been building major Rails apps since 2006.
So that clinched it.