Next year marks the 50th anniversary of the detection of Coronal Mass Ejections from space. The discovery and subsequent observations of thousands of events from a stream of coronagraph telescopes marked a paradigm shift of our view of the corona, from a physical system changing gradually over a solar cycle, to a system marked with explosive transient activity on timescales from seconds to days to months. Thanks to coronagraphs, and more recently EUV imagers, Space Weather forecasting and research have become strong research areas within the Heliophysics discipline. adding to that, the transients and even the more quiescent background wind can now be imaged directly in the inner heliosphere thanks to the advent of heliospheric imaging since the mid-2000s. The recent deployment of the Parker Solar Probe and Solar Orbiter missions ushers a new era of coronal/heliospheric imaging from widely varying vantage points along with future missions, such as PUNCH, and operational mission at the L1 and L5 point. It is, therefore, an appropriate time to take stock of the lessons learned from the decades of imaging of the solar wind, both quiescent and transient. In this talk, I review those lessons/learned and discuss where to go next.