i would think summer 2015 would be a good start
Well, I'm going to ad-lib and go back to end of reg season 2015 if that's ok with you.
I do not extend Sbisa or Dorsett before the playoffs.
I do not trade Bonino, I see him as a valuable piece in a re-tool, and at his salary he could be moved to a contender for futures at the 16 or 17 deadline, but in the meantime, a perfect stop gap while waiting for Bo.
I still trade Bieksa. I use the 2nd at the draft.
I keep Eddie Lack, moving the sought after Ryan Miller for a better return than Lack received. .
I extend Brad Richardson for similar contract to what he got in Arizona.
I don't keep McCann or Virtanen past 9 games. I probably keep Vrbata with the Twins.
I run a lean bottom 6 using the in house veterans and some of the cheap depth in the org (Gaunce etc).
I don't trade for Granlund, I look to continually target the age gap, but for free on the waiver wire....I pick up Sven Andrighetto instead.
I target undervalued free agents on short term deals. I'm willing to pay higher salaries for the flexibility of not adding term. I can't recall all of the available free agents over those years, but if we could get Vrbata and Miller by offering the best contracts, I'm sure I could've done the same on others.
I don't add at the deadline if I'm in the hunt, but I also look to use the cap space I saved as opportunity to pull in good players with picks, who due to salaries are no longer wanted by their current team.
I don't know how much further to take this, but at worst I finish with the same record or slightly worse (you can only go down 2 places for 3rd worst). Which is kind of the entire point right....they attempted to retool, their own moves fell flat and they ended up as the worst team over the 3 years.