...If I had 50K to drop on a sedan, that would open a lot of doors. I second the opinion on the BMW 5-series. Not really big, but worth every penny. Also, I would consider the new Caddy STS. With the Northstar, four wheel independent suspension that was tuned on the 'ring and rwd, it's supposed to be a fine drive. Lincoln LS is often overlooked, too. It's better than a lot of people give it credit for, and in its final year, I am sure you could work a heck of a deal on a loaded one. A loaded Acura TL would be tempting, and again, you would have money to spare. Acura RL fits the bill, too. An Audi A6 would be tempting, as would a Mercedes C or E class. There are so many good choices, (and a lot of them fun to drive) but ultimately it's all going to boil down to which one he likes the best during the test drives.