Bought my sons at Play it Again sports. Already broken in. First one we bought was brand new, and a 5 year old will never be able to break it in by playing catch, because they can't catch. Just don't buy one of the tiny ones that a ball can barely fit in, they are always too stiff and essentially useless.
This is where I am at...my son, got a new glove from grandma...it is a nice wilson glove...but it is stiff...
He isn't skilled enough a the moment to catch a ball (he has his dad's abilities

) which is why I want to try to expedite the process of breaking it in to hopefully make it easier for him to learn the ropes of catching fly balls (little ones) and grounders...
Thanks much for the recommendations, I plan on getting some of the glove oil...doing the Rubber band with ball trick in the oven and manual manipulation...
What temp do you generally put it in the oven at and for how long?
Thanks again guys,
Lee