This present study investigates the development of second language (L2) Chinese learners’ writing by 1) subjective ratings of essay quality, 2) a battery of objective measures representing the general syntactic complexity as well as specific syntactic features, and 3) the sources of verb phrase complexity used by learners of different institutional levels. This study first compares the subjective ratings of the essays written by learners across four institutional levels and then uses Cumulative Linked Model to examine the contribution of the objective measures of linguistic features to the essay ratings. This study further identifies a number of sources used by learners to construct complex verb phrases, which is an important contributor of the essay rating, and compares the amount of usages by learners at different institutional levels. The purpose of the study is to better understand L2 Chinese learners’ syntactic development in writing from multi-dimensional perspectives, and to identify the most crucial elements that determine the quality of writing. This study recruits 105 L2 Chinese college learners to write a narrative essay and an argumentative essay according to the prompts. Each of the writing sample is rated by two independent raters according to the holistic ACTFL Proficiency Guidelines, as well as the analytic rubric which was adapted from the ESL Composition Profile for this study. The derivation of syntactic complexity measures was based on the rank scales of lexicogrammar in Systemic Functional Linguistics (Halliday & Matthiessen, 2014), involving 12 features at the levels of clause complex, clause, and verb phrase, some of which represent constructions unique to Chinese. A series of statistical tests, including Kruskal-Wallis tests, Dunn’ tests, Spearman’ correlation tests, and CLM are performed to answer that research questions. The findings show that 1) learners’ overall writing quality measured by holistic and analytic ratings do not show significant differences across the first several academic years; 2) higher-level learners are more heterogeneous in writing ability than lower-level learners; 3) phrasal complexity contributes more to the essay quality than clausal complexity; 4) syntactic complexity features that learners develop fastest hardly overlap with those that contribute most to the essay rating; 5) complex verbal phrases come from 10 different sources and the composition of complex verbal phrases remain stable across the groups; and 6) essay types makes significant differences in terms of holistic and analytic ratings, use of syntactic complexity features, as well as their contribution to the essay ratings. From the pedagogical view, this study points out that instruction should focus more on complexity at the phrasal level, especially nominalization and complex verb phrases, that play a more important role to determine the writing quality. Some of the current focus in instruction may not necessarily lead to better quality or higher proficiency in Chinese writing.