Background: During grammatical treatment of children with developmental language disorder (DLD), it is natural for therapists to focus on the grammatical details of the target language that give the children special difficulty. However, along with the language-specific features of the target (e.g., for English, add -s to verbs in present tense, third-person singular contexts), there are overarching factors that operate to render the children's learning task more, or less, challenging, depending on the particular target. Aims: To identify five such factors that can play a role in the grammatical learning of children with DLD. We use English as our example language and provide supporting evidence from a variety of other languages. Main Contribution: We show that the relative degree of English-speaking children's difficulty with particular grammatical details can be affected by the extent to which these details involve--(1) bare stems; (2) opportunities for grammatical case confusion; (3) prosodic challenges; (4) grammatical and lexical aspect; and (5) deviations from canonical word order. Conclusions: During treatment, therapists will want to consider not only the English-specific features of grammatical targets but also how these more general factors can be taken into account to increase the children's success.