This Friday, I hit the friendly skies to Cabo San Lucas. I can’t wait to go. I haven't been anywhere noteworthy in a while. I can picture it now: the beach, the sun, the all-inclusive food and booze. It's definitely going down. While I'm eager to get going, I'm dreading the packing process. I never know what to take and often have a hard time figuring out what I want to wear while I’m out of town. My usual packing method: The night before trip, open suitcase, dump in loads of clothes, shoes, and toiletries, sit on suitcase until it's closed tight enough to zip up. The End. But I'm a man of a certain age now. And it's time I left those childish packing antics behind. Besides, it's too expensive to check a bag these days. Last summer, it cost me $50 to check my luggage on a round trip flight to Chicago. To avoid future check-in fees and get my suitcase packing game on point, I enlisted the help of quintessential packing expert Doug Dyment. Dy...