Ryan Pike actually did a write-up on Flames Nation about a week ago about our head-coaches since the '04 lockout that's a good read.
Dutter: We apparently spent some money here (and had a ton of experience). Though he was also GM, and that was likely a factor in his salary being higher
Playfair: First time HC, probably dirty cheap
Mike Keenan: Cost a fair bit of money
Butter: While maybe not "expensive", was likely not cheap
Hartley: Former cup winner, likely not cheap
Gully: Second time HC (first time was that stint in Dallas), probably cheap
Peters: Not cheap, but not expensive.
Ward: Cheap, but got a raise when taking the interim title (and likely another raise when made official HC)
He then analyzes amount of Conference Final appearances, and basically states "Spending big on a veteran coach only works in the right situations, and is a costly backfire otherwise." The only veteran coaches to have success before actually winning the cup were Quennville and Dutter (Q with 11 seasons under his belt before going to Chicago, Dutter with 12 before going to LA). DeBoer, Lavi, Babcock, and Vigneault were all cases where they were given a second chance after their first gig was unimpressive at best (similar to Gully and Peters for us). Cooper, and Carlyle (first time in Anaheim) were both first time head coaches when they started having success. Basically, there is no sure-fire way, and it has to be done on a case-by-case basis. Do the coaches work with the way the team is built, can the coach get a good rapport with the players (doesn't have to be friends, but at least a strong working relationship that is amicable), and in a couple cases, can the team get lucky under that coach.