We present a multi-wavelength analysis of three compact galaxy groups, HCGs 16, 22, and 42, which describe a sequence in terms of gas richness, from space- (Swift, HST, Spitzer) and ground-based (LCO, CTIO) imaging and spectroscopy. We study various signs of past interactions including a faint, dusty tidal feature about HCG 16A, which we tentatively age-date at <1 Gyr. This represents the possible detection of a tidal feature at the end of its phase of optical observability. Our HST images also resolve what were thought to be double nuclei in HCG 16C and D into multiple, distinct sources, likely to be star clusters. Beyond our phenomenological treatment, we focus primarily on contrasting the stellar populations across these three groups. The star clusters show a remarkable intermediate-age population in HCG 22, and identify the time at which star formation was quenched in HCG 42. We also search for dwarf galaxies at accordant redshifts. The inclusion of 33 members and 27 associates (possible members) radically changes group dynamical masses, which in turn may affect previous evolutionary classifications. The extended membership paints a picture of relative isolation in HCGs 16 and 22, but shows HCG 42 to be part of a larger structure, following a dichotomy expected from recent studies. We conclude that (a) star cluster populations provide an excellent metric of evolutionary state, as they can age-date the past epochs of star formation; and (b) the extended dwarf galaxy population must be considered in assessing the dynamical state of a compact group.