There is now substantial evidence that the progenitors of some core-collapse supernovae undergo enhanced or extreme mass loss prior to explosion. The imprint of this mass loss is observed in the spectra and dynamics of the expanding blastwave on timescales of days to years after core-collapse, and the effects on the spectral and dynamical evolution may linger long after the supernova has evolved into the remnant stage. In this paper, we present for the first time, largely self-consistent end-to-end simulations for the evolution of a massive star from the pre-main sequence, up to and through core collapse, and into the remnant phase. We present three models and compare and contrast how the progenitor mass loss history impacts the dynamics and spectral evolution of the supernovae and supernova remnants. We study a model which only includes steady mass loss, a model with enhanced mass loss over a period of $sim$ 5000 years prior to core-collapse, and a model with extreme mass loss over a period of $sim$ 500 years prior to core collapse. The models are not meant to address any particular supernova or supernova remnant, but rather to highlight the important role that the progenitor evolution plays in the observable qualities of supernovae and supernova remnants. Through comparisons of these three different progenitor evolution scenarios, we find that the mass loss in late stages (during and after core carbon burning) can have a profound impact on the dynamics and spectral evolution of the supernova remnant centuries after core-collapse.