Distributed energy resources (DERs) are transforming the operation and planning of both distribution and transmission grids. Stability impacts from the increasing generation contribution of DERs have been widely recognized in distribution systems and are emerging in transmission systems. There is a need for the development of transmission hosting capacity studies of DERs so utilities will be able to predict and prevent instabilities, reductions in reliability on the electrical grid, and create planning methodologies that enable the continued growth of DERs. This paper evaluates the impact of different modeling considerations for assessing hosting capacity of DERs in transmission systems through analysis on a 2,000-bus synthetic grid test system. The modeling considerations include transient and steady state contingencies, use of dynamic load and DER models with voltage support control, dynamic load composition, and seasonal and loading scenarios. The results demonstrate that transient stability evaluations are more limiting than steady state analysis, the use of voltage support control in DERs can increase hosting capacity in the system, and large variations in hosting capacity can be found when assessing between seasonal variations. From comparing system factors the amount of wind generation in the system was a critical factor for hosting capacity in this study.