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Both at once. Your suffering/regret will be less than the aggregate of doing it in two separate events, and the younger dog is not "young," nor likely to get better. In fact, you're likely to have to watch the younger dog mourn and get worse.
Sucks. Good luck, bud.
JP
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2003 SuperCharged Frontier ../.. 1979 930 ../.. 1989 BMW 325iX ../.. 1988 BMW M5 ../.. 1973 BMW 2002 ../..1969 Alfa Boattail Spyder ../.. 1961 Morris Mini Cooper ../..2002 Aprilia RSV Mille ../.. 1985 Moto Guzzi LMIII cafe ../.. 2005 Kawasaki Brute Force 750
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