The crux of this argument is that we overpay for guys then in 2 years that overpay is now a good contract.
It is never good to "overpay" thats by definition bad business, however we dont want to overpay middleton or anyone else, but you can pay based on 2 years from nows cap rather than todays.
Is sacrificing two years of flexibility with an over-market value contract worth it, to get a guy under contract for (hopefully) fair value in the last two years?
That seems like a silly gamble to me. If the best case scenario is that we overspent for 50% of the contract, and there's no possibility that Middleton will be a bargain, how is that good for us? That's without even considering the downside of regression, which is certainly a possibility with a guy who has only been a good defender for one season, in a contract year in a defense-first system.
Signing Middleton to this type of contract does not sacrifice your flexibility. That's the main gist in all of this, this is a risk worth taking because the consequences of failure are minimal.
Let's say we strike out on all our targets, and we can only get Middleton on that type of contract, we should still have about $35-$41 or so million (I'm really throwing numbers around here, as haven't have the time to really breakdown the 2016 salary situation) of cap space to work with next Summer. And keep in mind that I'm not discounting the QO's and team options we may have.
I mean, if that's not flexibility, I don't know what it is then. Going forward our guaranteed commitments are very very low. Spending on Middleton will not damper us any, and might actually open up opportunities for us.
In the following years, with the increase in salary cap (and of player contracts), that's when we have to be more careful on our usage, but not this Summer.