We present an observational study of the Type IIn supernovae (SNe IIn) 2005ip and 2006jd. Broadband UV, optical, and near-IR photometry, and visual-wavelength spectroscopy of SN 2005ip complement and extend upon published observations to 6.5 years past discovery. Our observations of SN 2006jd extend from UV to mid-infrared wavelengths, and like SN 2005ip, are compared to reported X-ray measurements to understand the nature of the progenitor. Both objects display a number of similarities with the 1988Z-like subclass of SN IIn including (1) remarkably similar early- and late-phase optical spectra, (2) a variety of high-ionization coronal lines, (3) long-duration optical and near-IR emission, and (4) evidence of cold and warm dust components. However, diversity is apparent, including an unprecedented late-time r-band excess in SN 2006jd. The observed differences are attributed to differences between the mass-loss history of the progenitor stars. We conclude that the progenitor of SN 2006jd likely experienced a significant mass-loss event during its pre-SN evolution akin to the great 19th century eruption of η Carinae. Contrarily, as advocated by Smith et al., the circumstellar environment of SN 2005ip is found to be more consistent with a clumpy wind progenitor.