Methods and apparatus to monitor work vehicles and to generate worklists to order the repair of such work vehicles should a machine failure be identified are disclosed. An apparatus includes an interface to access a first and second alerts from first and second work vehicle; an alert scorer to generate first and second scores for the respective first and second alerts; a machine health score determiner to determine first and second machine health score for the respective first and second work vehicles based on the first score and the first weighting factor and the second score and the second weighting factor; and a worklist generator to generate a worklist indicating that the second work vehicle is to be repaired prior to the first work vehicle based on at least one of the first and second machine health scores or an associated first and second classifications.