Katharevousa Greek remains poorly served by contemporary NLP pipelines despite its importance for legal, administrative, and parliamentary archives. We present a reproducible workflow for building and evaluating a Universal Dependencies-style parsing resource for Katharevousa parliamentary questions from Greece's early post-junta period. The pipeline links OCR-aware reconstruction, schema-constrained LLM-assisted annotation, automatic validation, deterministic CoNLL-U snapshotting, fixed-split evaluation, and model-family comparison. The frozen automatically validated reference set contains 1{,}697 sentences, split into 1{,}357 training sentences and 340 held-out test sentences. We compare off-the-shelf Greek and Ancient Greek parsers, a feature-based parser, mBERT, XLM-R, and custom Stanza training under the same scoring protocol. Off-the-shelf systems show substantial register mismatch: the strongest external baseline, spaCy Greek, reaches 0.4183 LAS. The best structural parser, an XLM-R model, reaches 0.8893 UPOS accuracy, 0.7250 dependency-relation F1, 0.6098 UAS, and 0.5162 LAS, an absolute LAS gain of 0.0980 over the best external baseline. The feature-based model remains competitive for UPOS and relation labeling, indicating that transparent lexical-context features still matter at this data scale. Beyond scores, the paper contributes an auditable methodology for turning difficult historical parliamentary OCR into reusable syntactic NLP infrastructure. The entire pipeline -- code, schema, frozen reference annotations, fixed train/test split, and per-model benchmark reports -- is released as an open-access companion to this paper.