You may not like this (and I know you are smart enough to know better) but I think that's exactly how Darryl Sutter started this cap mess we are currently in, ie."I like this player so paying 1 mil or so over to retain him is small potatoes..." multiplied by several players... then those players didn't pan out like he hoped and there is no recourse to deal them because we don't have the cap flexibility to deal with their negative trade value.
JBo is impressing me (finally) and I agree that paying a little more to retain him through a rebuild is not a bad idea if we are in a position to do that but there is some serious maneuvering that needs to be done before we can honor all existing contracts and still fill out a semi-competitive roster next year. Of course dealing core members before the start of next season and Daymond Langkow's career status would have an affect on the direction you go with JBo but I don't think you can count on gaining much cap space in any deals involving Regehr, Kiprusoff or Iggy simply because most teams can't afford to put themselves in the same position as the Flames are in by trading their high picks/prospects for big dollar, multiyear contract players who will likely not be earning their cap hit in the latter part of their deals and don't guarantee cup success, the majority of teams will know we are not dealing from strength and will insist on sending cap back.
The Flames are the poster children of cap mismanagement in the new NHL (save maybe New Jersey) We have shown why you can't afford to spend recklessly on long shots with precious cap money like Dutter has. The common thinking would be that the more prospect talent you have in the system and/or the more upcoming top end draft picks and/or the more cap space you have, the more risks you can take in overpaying certain players to fill key roles on the team to win now. This is where I get really upset and confused at the risks that Dutter has taken with our future. With our high end prospects/draft picks being severely depleted and no cap space reserved as an insurance policy, he acquired some cap significant multiyear contracts to fix what he thought was broken that were as far from being sure things as you can get. I think when you are figuratively working without a net, you should play it safe and bide your time and wait for a high percentage opportunity to present itself, in other words, don't bet the farm on a flip of a coin. (The Phaneuf deal, the Rangers deal)
I like the strategy of "win now" and building to be perennially competitive but not at the cost of putting the team at serious risk of multiyear catastrophic failure and it appears to me that in his ego driven obsession to prove he was right all along, Darryl Sutter has put the team into that very position as sure as if he had drawn up blueprints with those intentions in mind. His only choices to move disappointing contracts are to take back equally unproductive overpaid contracts in trade (why?), utilize cap space to sell at a loss (we don't have cap space), or stand pat and painfully ride out the duration of the contract(s). He must pray every night that the angry mob doesn't beat down his door while he waits for some miracle prospect to drop into his lap like manna from heaven or dream that like in a B rated late night zombie movie, the dead half of the team rises and starts playing like they are some unstoppable hockey monsters with a blood thirst for the Stanley Cup.
While I don't disagree with your theoretical assessment of our D core moving forward, I think that this team's ability to overpay for anyone is severely limited.