Using multiple treebanks to improve parsing performance has shown positive results. However, to what extent similar, yet competing annotation decisions play in parser behavior is unclear. We investigate this within a multi-task learning (MTL) dependency parser setup on two parallel treebanks, UD and SUD, which, while possessing similar annotation schemes, differ in specific linguistic annotation preferences. We perform a set of experiments with different MTL architectural choices, comparing performance across various input embeddings. We find languages tend to pattern in loose typological associations, but generally the performance within an MTL setting is lower than single model baseline parsers for each annotation scheme. The main contributing factor seems to be the competing syntactic annotation information shared between treebanks in an MTL setting, which is shown in experiments against differently annotated treebanks. This suggests that the impact of how the signal is encoded for annotations and its influence on possible negative transfer is more important than that of the input embeddings in an MTL setting.