Next tim yu're mixing tequila with fresh grapefruit juice try Cuervo Traditional. Surprising good, especially with fruit juice. Save the "Good Stuff" for rocks or shots.
IMHO, I would pair the Barolo with Tenderloin or better yet, a thick cut Delmonico. Save the Amarone, underrated for after dinner. Serve a little chilled and enjoy this more sweet Italian red.
Hard to find. However you can't go wrong with any of these Antinori wines: Tignanello is very good and Gaudo Al Tasso is my favorite. Solaia is even better. Angelo Gaga's wines, especially his single vineyard Barbaresco is very pricey but why not for special occasions ;-)