Letters to the Editor
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A short answer
I volunteer at the SPCA. Small dogs fly out of there, especially if they are cute and personable. I suspect even an older dog, like an 11 year old Yorkie, would find a home very quickly.
I recommend going through a responsible animal rescue with the dog, rather than craigslist or freecycle. They'll suss out the potential owner's ability to care for the dog and offer an option of taking the dog back if things don't work out.
The rest of it, the emotional stuff, you can deal with. But don't feel bad about the dog. If you can't care for him, then a shelter will.