When Should I Drink That Wine? A Question of Aging

A reader named Chris recently wrote in looking for guidance about whether to drink or age the wines in his collection. I imagined many readers might have similar questions or concerns from time to time, so here's Chris' question, along with my response:
I have about 25 mixed cases of wine, mostly cabs and red blends, mostly Californian, ranging from the late 1980s right up to the 2010 vintage. Ridge, Beringer, Cakebread, Heitz, Caymus, Dunn, Baldacci, Black Sears, Pahlmayer, Grgich, Bell, Mount Veeder, Hess Collection, Von Strasser, Gargiulo, Larkmead, Vine Cliff, Laird, PIna, etc. Are there people out there who are prepared to give free advice about what to drink up and what to sit on for a while longer? Can you point me in the right direction?