Dash Rendar and Prince Xizor. Everyone is always dismissing Dash Rendar as discount Han Solo, but I still think he could work, make him more ruthless and far more driven by material gain.
Clan Ordo of the Mandalorian.
The Old Republic era.
Dash would work really well in an environment like The Mandalorian, and with the way Dave loves the implement legends material, we could see him in the near future.
The Old republic will 100% appear in canon again. The High Republic is the current goal at Lucasfilm & I feel it is a worthy successor to the OLD old Republic we know from legends.