I toyed with this idea as well. I'm always afraid that Zoe is lonely. I also know that another dog means more responsibility as well as more money. I joined a NYC yorkie meet up group and as soon as it gets warmer, I will start taking Zoe on meets. There is also a doggie park by my house that I am going to bring him.
I think that Cassie is completely content with you alone but if you feel like she should have a pal then so be it but from the sounds of your thread there are some doubts so I would suggest arranging some playdates before making your final decision.
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