Retool priorities:
We have 3 1B/DH players. Pearce can play LF but he's not very good there. Ideally, Morales would be traded, but that might be difficult. So I think trading one of Pearce or Smoak would be dealing from a position of relative strength.
I think Happ should be traded if there's a decent offer out there. He's only got one more season on his contract and his age = higher risk of decline next year.
In the offseason JD either signs a team friendly deal (i.e. much less than $30m for 5+ seasons) or is traded for multiple assets, including at least one player who can play straight away.
Use August/September this year to see if players like Alford, Smith Jr, Pompey (possibly Gurriel and some of the pitchers) should be on the 25 man next year. Plus see if Travis comes back this season.
Trade Estrada and Liriano and move Biagini back to starting again as an audition for next year.