I do something that might sound odd.

If there is a free checked bag, depending on carrier, I will bring a medium sized suitcase, a carryon bag and if it's business, a laptop bag.

The suitcase is empty. I will pack a box of twinkies and a couple shirts in it at most. On the way back, if the shopping was good, the forty dollar dresses for my niece and the hundred dollar jacket for my nephew go in the suitcase. If it's lost, no big deal. But if I get to my location, I then stuff my carryon bag into the suitcase, so I'm then only handling two bags (suitcase and laptop bag) and it's a heck of a lot easier to manage.

I stopped bringing three suits, all the shirts I owned and three pair of shoes for a weekend trip. If I can't get by with a seersucker blazer and a dark suit, I probably should reconsider what I'm spending on that weekend. Therefore even if the suitcase is free, it contains the minimums.

Also, I require regular liver medication. If I get separated from my pills, bad things can happen. I don't take that risk. I've never heard of an airline losing my carryon.

C.