Objective: Surveillance imaging of chronic aortic diseases, such as dissections, relies on obtaining and comparing cross-sectional diameter measurements at predefined aortic landmarks, over time. Due to a lack of robust tools, the orientation of the cross-sectional planes is defined manually by highly trained operators. We show how manual annotations routinely collected in a clinic can be efficiently used to ease this task, despite the presence of a non-negligible interoperator variability in the measurements. Impact: Ill-posed but repetitive imaging tasks can be eased or automated by leveraging imperfect, retrospective clinical annotations. Methodology: In this work, we combine convolutional neural networks and uncertainty quantification methods to predict the orientation of such cross-sectional planes. We use clinical data randomly processed by 11 operators for training, and test on a smaller set processed by 3 independent operators to assess interoperator variability. Results: Our analysis shows that manual selection of cross-sectional planes is characterized by 95% limits of agreement (LOA) of $10.6^\circ$ and $21.4^\circ$ per angle. Our method showed to decrease static error by $3.57^\circ$ ($40.2$%) and $4.11^\circ$ ($32.8$%) against state of the art and LOA by $5.4^\circ$ ($49.0$%) and $16.0^\circ$ ($74.6$%) against manual processing. Conclusion: This suggests that pre-existing annotations can be an inexpensive resource in clinics to ease ill-posed and repetitive tasks like cross-section extraction for surveillance of aortic dissections.