Friendly reminder - guys like Rafael Addison, Dave Johnson, Jason Cipolla, Marius Janulis and Stevie Thompson all played time as shooting guard for us. We even tried Stevie at point. I don't think any of those guys had a decent handle at all, certainly not good enough for a guard.
But if you had an excellent PG who could beat a press by himself (Pearl, Sherm, Jonny Flynn), and if you had a forward or two with a handle (like Owens, Coleman, Wallace, etc.), then you can get away with playing guys a bit out of position, in order to get the benefit of a particular skill that guy provides.