Just based on some of the comments I've seen:
Holmgren's best off-season was the one where Rathje got hurt and never really played again, and in turn he got to spend a lot of money. That was 6 years ago by the way. Less than 5 into Clarke's 2nd reign as GM had people on talk radio boycotting the team until he was fired or resigned. Don't forget that the Flyers also essentially traded a late 1st (1st pick in the 2nd round) for a goaltender that they could have signed had they simply waited a few months. Since then, has Holmgren "won" an off-season?
The Flyers weren't in that bad of a position in 2007. They still had Richards, Carter, Umberger, Gagne, Knuble, Downie, Pitkanen (traded for Lupul) and they had just drafted Giroux. An objective analysis of the team at the time, and not simple conjecture from TSN experts, whose opinions shouldn't hold any more or less water than your own, would see that. They had a bad year. It happens. It's supposed to happen when there is supposed to be league-wide parity. Over the most recent CBA, only two teams made the playoffs every year, one team missed every year, and no one finished higher than 5th every year.
Regardless, constantly trading away young players for the now-players past their primes and never being patient or having any sense of organizational development is how you get to be the St. Louis Blues of the 90s. They always made the playoffs, but were never a contender.
By the way, if you go back to when Holmgren was hired, Clarke said himself that Holmgren was largely responsible for the moves made into 2006-07. It's one of the reasons why he wasn't Snider's first choice to replace Clarke.
Also, the return for Forsberg is one of the more overrated gems of Holmgren's work. He looked good in making the trade, but didn't make the results count. Traded the 1st back just to sign Timonen and Hartnell before free agency (it worked out, but it was a trade made out of paranoia and not savvy), traded the 3rd to draft Kevin Marshall, traded Upshall *with* a 2nd round pick for Carcillo (terrible if not pointless). The best part of that trade was duping the Penguins into taking Hamhuis' rights after we traded Ryan Parent for it, which led to signing Bryzgalov.
Holmgren working within the organization for almost 20 years is directly responsible for always having to overpay in signing or trading for defenseman, having been an abject failure in drafting them. The Flyers have not drafted and kept a defenseman on their roster for as long as Holmgren has been here.