Despite both printings being shadowless, usually only the 2nd printing is referred to as shadowless, as it is easier to differentiate the 1st printing by its Edition 1 logo
Roscinante sweet spot: your leader ability prevents the opponent from killing your Sugar or Baby5 Tutor
That means my wide range of interesting one-drop creatures could come in very handy if I'm not just getting a single six-drop like Massacre Wurm or Conquering Manticore
Tapping a creature when he attacks is good, and getting bigger with each artifact you play can be nice, but with no evasion and no protection he's likely to just get removed before you have a chance to do anything
Dark Confidants downside is negligible in these matchups, and while it doesnt interact itself, it does ensure that you see enough cards to be able to present the necessary quantity of interaction while still consistently pressuring their life total
Even in a "bad" use case, if a player has three to five creatures in play, they can give each of them trample, vigilance, and a +1/+1 counter to push damage through