Comment by Terr_
I often find myself wishing for a Checked Exceptions, I think things would have played out differently if there was more syntactic sugar.
Like if one could easily specify that within a certain scope (method or try-block), any of a list of exception classes (checked or unchecked) will become automatically wrapped into a target checked exception class as the chained "cause."
So you could set a policy that EngineBrokenException=or OutOfFuelException bubbling up will become FleetVehicleInoperableException.