In this paper, we present the annotation challenges we have encountered when working on a historical language that was undergoing elaboration processes. We especially focus on syntactic ambiguity and gradience in Middle Low German, which causes uncertainty to some extent. Since current annotation tools consider construction contexts and the dynamics of the grammaticalization only partially, we plan to extend CorA - a web-based annotation tool for historical and other non-standard language data - to capture elaboration phenomena and annotator unsureness. Moreover, we seek to interactively learn morphological as well as syntactic annotations.

We provide a robust and detailed annotation scheme for information status, which is easy to use, follows a semantic rather than cognitive motivation, and achieves reasonable inter-annotator scores. Our annotation scheme is based on two main assumptions: firstly, that information status strongly depends on (in)definiteness, and secondly, that it ought to be understood as a property of referents rather than words. Therefore, our scheme banks on overt (in)definiteness marking and provides different categories for each class. Definites are grouped according to the information source by which the referent is identified. A special aspect of the scheme is that non-anaphoric expressions (e.g.\ names) are classified as to whether their referents are likely to be known or unknown to an expected audience. The annotation scheme provides a solution for annotating complex nominal expressions which may recursively contain embedded expressions. In annotating a corpus of German radio news bulletins, a kappa score of .66 for the full scheme was achieved, a core scheme of six top-level categories yields kappa = .78.