I'll try to ignore for a moment the extreme inconvenience to other passengers, delays in boarding, etc, of such items when used as what is referred to in this part of the world as "hand luggage", except to mention that anything big enough to be on wheels will thankfully not be allowed on many airlines outside the USA. (Try it in New Zealand and see how far you get. <g> )
One thing I've wondered about all luggage: Is it worth getting good stuff, especially for hand luggage? There are decently designed no-name cheapies for 1/10 the cost of a Samsonite which can last for more than 1/10 the time and don't give you cause to worry about possible damage to them.