This article presents the results of a pilot survey of 300 transport operators, such as drivers, train drivers, and rescue workers. The surveys were conducted online using a Google form based on the Computer-Assisted Web Interview (CAWI) method. The following research objectives were set: to identify and compare the most relevant factors affecting the health and wellbeing of transport vehicle operators and to identify the key risks associated with their work. The findings were presented using descriptive statistics and correlation and principal component analyses. Descriptive characteristics indicated which quantitative characteristics were associated with exposure and discomfort. On the other hand, the results of correlation analyses showed, among other things, that “level of rest” as a function of “fatigue” showed a decreasing relationship and that “pain in arms, legs, lower back or neck” depended on “work position,” “use of excessive force,” and “work severity.” The results of the principal component analysis confirmed that the data cluster under the form of factors and that there are factors whose information values are insignificant. A similar conclusion applies to the input data (i.e., the answers to the test questions). The analysis showed that only the answers to 15 of 50 questions exceeded the threshold of 2% of the information entered in the test. This could lead to the conclusion that if the test could be repeated in the future, the correct result might be obtained with slightly fewer test questions.