My challenge is the time required to do the shopping when a bag is lost. Last time this happened, I was traveling to Singapore for work (with a checked bag) and ended up spending my first afternoon on arrival running around malls looking for clothes that would fit me for the week of business meetings I had. Since that experience, I'm HBO no matter the length of the trip if it's for work.

Now, for personal travel where I'm not on the clock, I'm happy to check the bag and cool my jets at baggage claim without a care in the world! My retired mother does the same on all of her trips as well.