In order to place constraints on cosmology through optical surveys of galaxy clusters, one must first understand the properties of those clusters. To this end, we introduce the Mass Analysis Tool for Chandra (MATCha), a pipeline that uses a parallellized algorithm to analyze archival Chandra data. MATCha simultaneously calculates X-ray temperatures and luminosities and performs centering measurements for hundreds of potential galaxy clusters using archival X-ray exposures. We run MATCha on the redMaPPer SDSS DR8 cluster catalog and use MATCha's output X-ray temperatures and luminosities to analyze the galaxy cluster temperature-richness, luminosity-richness, luminosity-temperature, and temperature-luminosity scaling relations. We detect 447 clusters and determine 246 r_2500_ temperatures across all redshifts. Within 0.1<z<0.35, we find that r_2500_ T_X_ scales with optical richness ({lambda}) as ln(k_B_T_X_/1.0keV)=(0.52+/-0.05)ln({lambda}/70)+(1.85+/-0.03) with an intrinsic scatter of 0.27+/-0.02 (1{sigma}). We investigate the distribution of offsets between the X-ray center and redMaPPer center within 0.1<z<0.35, finding that 68.3%+/-6.5% of clusters are well-centered. However, we find a broad tail of large offsets in this distribution, and we explore some of the causes of redMaPPer miscentering.