You do have one of the suckiest situations.
My decision is a lot easier. I'm on a share plan, didn't use my Premier upgrade (surprise), and my 22-mo multi-line upgrade comes up in July. If I take the upgrade now, my wife's phone will be 3yro before we qualify for another subsidy. So I'm waiting until July so we can both get phone upgrades.
The downside is that instead of having one $10/mo smartphone surcharge, we'll have 2.