After thinking it over more, the FO may view us as having two separate windows. I've said that I don't believe our natural window will start opening until 2018. So the FO may be trying to open one from 2016-2019 or so before all of our best talent starts hitting the team.
If Heyward does want to sign a shorter deal in order to hit FA again at 30 or 31, I would go get him for 5 or 6 years. If you can get him for that at $25 million per year or less, I would do it. That would also leave us room to sign a good SP, like a Kazmir to a 4- or 5-year deal. That would give us the following major league pieces:
Freeman - signed through 2021
Simmons - signed through 2020
Heyward - signed through 2020/2021
Peterson - under control through 2020
Olivera - signed through 2020
Bethancourt - under control through 2020
Markakis - signed through 2018
Maybin - signed through 2016/2017
Kazmir - signed through 2019/2020
Teheran - signed through 2020
Wisler - under control through 2020/2021
Miller - signed through 2018
While that may not be one of the top teams in baseball, it's a team that should compete and make a run at a playoff spot for 2016 and 2017. And if our payroll goes up to around 140-150 million by 2017, as I believe it will, you would also have a little more money to play with as well, though guys like Freeman start getting expensive at that point.
But that gives you a pretty clear window through 2020 with the guys already at the major league level, and as other talent starts to come up, like Mallex, Jenkins, Banuelos, possibly Ruiz, etc., you can supplement the roster with cheap options and also potentially make guys like Maybin and Teheran expendable in trades.
Then, as 2020 and 2021 hit, you start freeing up money again while letting these guys go as they hit the age where they should start regressing, and by then we will be in the middle of the Albies-Davidson-Toussaint wave with guys like Allard, Soroka, Riley, Yepez, Maitan, etc. ready to make an impact, which starts the new window with a really young team.
That's not a bad plan, and I hope our FO is seeing something similar.