Sid milestones are all we have left for a while.
Who helps that along the best? It's got to be B.Tkachuk and/or Marner.
The rest is all fun for armchair GMing but, without evening being pessimistic there is not a chance we do anything competitive for quite some time with the marriage to Sullivan AND his roster construction. As said before, sometimes you can just go against the grain and give Sullivan the opposite of what he wants and overcome a bad coach - but we let that dude literally run the entire organization and he's just not good at any one bit of that. His worst trait to me isn't coaching - it's scouting, call ups, and roster construction. I.e. he would be a downright putrid GM. Yet he's essentially ours.
As a side note. The Florida takes have been bizarre, off base, and quite bad. Is what it is though. My family has been here for a very long time (before Mr Walt "put it on the map") and the state's growth has been impressive. As with most places, the cities we have (outside of Miami) are our most undesirable locations. Nobody likes Tampa - but Clearwater? Orlando is shit, but have you seen the Butler Chain of lakes to the west of it (Arnold Palmer, Ken Griffey, formerly Shaq and a number of other hollywood second homes there). Jacksonville is like what Kat Williams said - has about 5 different 'hoods', is sprawled out and a whole lot of 'ehhh'... the best parts are areas one to two zip codes removed from those places, and that's often where the money ends up.