In the design of an embedded processor, the compiler design is tightly coupled with the underlying processor architecture, and thus it is crucial to rapidly retarget a compiler along with the change in the architecture in order to expedite the processor design. However, among many compiler writers, there is a controversial issue that has long been argued - whether a compiler can be easily retargetable while it performs sophisticated machine-specific optimizations for a new architecture configuration. This study examines this issue by finding some possible cases where optimizations may be impeded on a pathway to building a retargetable compiler. For this, we developed two types of compilation frameworks called user-retargetable and developer-retargetable, and compared their performance.