I usually check a bag because when I travel, even on business, I generally like to take advantage of whatever outdoor recreational opportunities (hiking, etc) might be available near my destination. For that reason I usually check a bag with boots and/or other gear.

I travel fairly regularly, but by and large I have not had a problem with lost baggage. Part of the reason may be that typically my trips are on a single airline with at most two flight legs. That being said, I always make it a habit to pack a minimum of stuff in my carryon to get me through at least two days at my destination. In my carryon I always have a couple of changes of undies, a clean shirt, etc. Some of the new easy care clothing made from synthetics is really handy, since in a pinch you can wash it in a hotel sink and it will dry overnight. One nice thing is that in today's more casual business environment I never need to wear a suit anymore.

The one time in recent memory where a bag did get lost (actually not lost bu only delayed for one day) was on a trip to Europe which involved multiple connections on multiple airlines. However, since I followed my usual practice of having the minimum I need in my carryon that was only a minor inconvenience.

I recently aquired an iPad mini, and I absolutely love it for travel. It is lightweight and compact, and I can check email, web surf, and even do minor word processing etc, without the hassle of carrying a laptop. These days when I travel my laptop stays at home, unless I know I will need it for some specific purpose. I realize other people have different requirements when they travel. In some lines of work a suit and tie is essential, as is a laptop. But for me a day pack and small brief case as carryon, and my old Eagle Creek rolling bag for checked luggage does the job, even on fairly long trips.