Getting Ready for Puppy: Adding A Second Pet

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It's 11:30 pm, and the latest addition to my family is wailing at the top of her lungs and sounding like a rabid cat. I'm reeeaally hoping my neighbors can't hear, but that could be wishful thinking. For the record, she's a 2 month old puppy; and we're doing Night 1: Crate Training.

[ Herbie and his new buddy. So far, they are not BFFs. Yet. ]

As Gregory put it succinctly, "Pets are just better in pairs." I agree, which is why, three years later, Herbie now has a sister. He hasn't quite warmed up to her yet (he peed on her during their introduction), but it's only been a day. Anyone have any tips for making the transition from one to two as smooth as possible?