The paper shows an advancement of the research that the authors have been carrying out in recent years in semantic structuring of digital architectural representations field, with a focus on the issue of uncertainty of annotations. The studies carried out in this regard have shown how the domain experts specialization determines a vision and interpretation of the same architectural object that we could define “categorized”. The interest was, then, in verifying which categories of experts have a greater degree of agreement in classifying and segmenting architectural elements, to highlight which specializations contribute the most in enriching the semantic reasoning about such forms. Aiming to broaden this reasoning, the research was deepened with annotation sessions concerning architecture examples that didn’t correspond to the classical orders rule but included wider fields of historical heritage (from sacred to fortified architecture). The aim is to verify whether the uncertainty of annotation is actually ascribable to a specific segment of the historical heritage, for example, the classical world, or whether the question is broader and as such in needs deeper thinking.