In this proceeding, we describe the scientific motivation and technical development of the Colorado High- resolution Echelle Stellar Spectrograph (CHESS), focusing on the hardware advancements and testing supporting the second flight of the payload (CHESS-2). CHESS is a far ultraviolet (FUV) rocket-borne instrument designed to study the atomic-to-molecular transitions within translucent cloud regions in the interstellar medium (ISM). CHESS is an objective f/12.4 echelle spectrograph with resolving power > 100,000 over the band pass 1000 - 1600 Å. The spectrograph was designed to employ an R2 echelle grating with "low" line density. We compare the FUV performance of experimental echelle etching processes (lithographically by LightSmyth, Inc. and etching via electron-beam technology by JPL Microdevices Laboratory) with traditional, mechanically-ruled gratings (Bach Research, Inc. and Richardson Gratings). The cross-dispersing grating, developed and ruled by Horiba Jobin-Yvon, is a holographically-ruled, "low" line density, powered optic with a toroidal surface curvature. Both gratings were coated with aluminum and lithium fluoride (Al+LiF) at Goddard Space Flight Center (GSFC). Results from final efficiency and reflectivity measurements for the optical components of CHESS-2 are presented. CHESS-2 utilizes a 40mm-diameter cross-strip anode readout microchannel plate (MCP) detector fabricated by Sensor Sciences, Inc., to achieve high spatial resolution with high count rate capabilities (global rates ~ 1 MHz). We present pre-flight laboratory spectra and calibration results. CHESS-2 launched on 21 February 2016 aboard NASA/CU sounding rocket mission 36.297 UG. We observed the intervening ISM material along the sightline to epsilon Per and present initial characterization of the column densities, temperature, and kinematics of atomic and molecular species in the observation.