I also gave Bear too much freedom in the beginning and he took a while to fully housebreak. I was VERY consistent though with taking him out. Rain, snow, wind...you name it, we went out in it. I also use a leash with Bear when we go out. He is now 11 months and I still don't want to chance it. I think Pockets may be too young to go off leash while outside.
...PS, she is adorable!!!