"There are many times when I walk into the showroom and think to myself, What the heck am I doing?" says Nick Alexander of his decision to sell his collection of 52 Ford and Mercury woodies this month. "But the pluses outweigh the minuses, and I’m keeping a few cars for myself." It’s no wonder Alexander won’t be parting with all of his beloved vehicles on the opening night of RM Auctions’ Sports & Classics of Monterey event (taking place August 13 through 15)—his love affair with this particular type of car has lasted for more than 50 years. Alexander began building his collection in 1995, but his interest was born when he started working for a Ford dealership at the age of 14. After spending a couple years completing predelivery services as a "get-ready boy" for the dealership, Alexander—then 16—paid $225 for his first woody, a 1951 Ford station wagon. During the four decades following that initial purchase, Alexander rose to success as a Southern California BMW and Mini dealer. Nick Alexander Imports (www.alexanderbmw.com) is just blocks from the circa-1908 industrial facility that currently houses his extensive collection of vehicles dating from 1932 to 1952. "They’re like children—you love them all, but there are definitely some I’ve spent more time with than others," says Alexander. Take, for example, a 1939 Ford that he drove to and from a Ford meet in Dearborn, Mich., where he ultimately received a coveted Dearborn Award for authentic restoration. Having decided to part with his wood-bodied babies—which range in estimated value from $20,000 to $350,000—Alexander says that he looks forward to spending more time at his Santa Ynez, Calif., ranch with his actual family, which includes four grandchildren.