This is an impossible subject to speak definitively about because many of the positive and negative outcomes of a GM's decision are dependent on a range of factors largely beyond their control, so a case by case basis either way is either cherry picking or at best indicative of minor trends. The only real test is overall results and overall comparisons to others.
First off, it has to be acknowledged that he inherited a great situation. Stacked roster, no salary cap, devoted fan-base, supportive owner and a ninja European scout. Could do a lot worse.
Equally, it has to be recognised that the job he did in extending that situation and improving the infrastructure around him surpassed all expectations. Anyone remember the wings being 'too old' and in terminal decline even before the salary cap was introduced? The wings dropping out of the playoffs within two years has been an annual prediction since the lockout over a decade ago. Hasn't happened.
Of course much of that has been dependent on coaching and drafting, neither of which he can take much direct credit for, particularly given our best draft picks have been late round specials. But crucially, the primary aspect of management is to find good people you trust and empower them with the trust and conditions to do their job well. This is perhaps, along with his patience, his biggest strength as a GM.
One also has to agree that although the post Lidstrom era has been less fun than hoped due to Suter's 50/50 choice being dictated by his ill advised decision to join his mate in the mountains, the Red Wings have done a remarkable job at circumnavigating the primary objectives of the combination of draft and salary cap, that being parity and a rotation of who makes the playoffs. Of course, a quicker route to the big prizes is to fail badly in good draft years, but the roster has remained too strong for this to be appropriate.
The over-riping development model, for the most part has been crucial to sustaining this. Because the team has remained at least partially competitive, it has been important to only rely on prospects when they are ready. If the team was in worse shape, they'd be up sooner.
And yes, the late round gems have kept on coming , from D & Z to the comparative huge successes (ie statistically massively overachieving compared for the norm for their draft location) of Hudker, Flip, Ericsson (and even Meech to a degree!) in '02, Quincey in '03 (though waiving him was such a poor choice at the time, he has eventually proved his worth), Franzen in '04, Abdelkader to a degree but certainly Helm in '05, (06 had real talent, but none made it here for different reasons), Andersson in '07 (just about..), Nyquist in '08, Tatar in '09 (and Jensen and Ferraro and Callahan may yet get there), Mrazel, Pulks in '10. Subsequent years have a very good chance to be equally successful or better, but its too early to say.
Howard (goalies are different!), kopecky, Smith & Sheahan are about par or just below at this point, and only really Kindl, Mccollum and maybe Emmerton are real disappointments.
Trading & FA is a bit more sketchy, but its important to balance recent years with earlier ones. Every Legwand (which if you prioritise the streak is a wash), Weiss, Tootoo, Modano, and the later Sammy/Cleary versions or even Robert Lang or Cujo if you want to be harsh is more than countered by Cleary/Sammy first time, Rafalski, Chelios, Larianov (second time I think was KH), Hull, Hasek (both!), Lucky Luc, Brad Stuart, Alfie, even drew Miller!
Also worth noting that barring the Robert Lang deal where Washington ended up with Mike Green, the wings have won on every single trade for draft picks or exchanging picks in the last 16 years. The only other exception was a pick that was eventually used for Patrick Sharp, but that changed hands about 4 times before the draft in which it was used!
The more recent trend is not that encouraging, but how many of the poor trades or FA signings have hamstrung us? Weiss is the only albatross, unless you decide that Howard's contract is as well, which is hardly a forgone conclusion given pre-injury performance levels. Of course the Franzen/Hossa thing will always be a frustration, but even despite people bagging him, until their is a cap reclaimation (NHL changing the rules AFTER the event), the Franzen contract has actually been mostly very good value.
Of course, what happens next is more important than what happened previously, and in the last 2 seasons the jury is out due to the unfortunate results of trades and Free Agency (such a shame about Cole, who looked a really nice fit in the top 9). So this summer is not insignificant. If Holland can bring in any quality FAs and get Kindl and Weiss of the cap, that would be success I think. but we can wait and see I guess.....
One thought I will leave with...imagine how much stronger his legacy would be if we hadn't seen the loss of Vladdy's norris levels of play, Fisher's punishing hitting or Grigorenko being seen as almost Kovalchuk good before his crash. We could easily be a cup or two better off.
Whether or not he could or should be replaced doesn't negate the fact that it's frustrating how poorly Holland has performed at acquiring NHL talent via trade or free agency. He's done a really lousy job of it for five years. Just because he drafts well doesn't mean that it's not colossally frustrating that he's made so many terrible signings and trades over the last five years.
I feel like I'm in the middle of the road on the issue at this point to be clear. I don't necessarily think he should be fired for what he's done given all that he brings in other areas, and I think he gets too much blame for a lot of things, but I can understand completely why he's become such a frustrating and polarizing GM. At this point, he's definitely deserving of much of the criticism he gets just as he's deserving of much of the praise that he gets.
I disagree with your premise though. I don't think he has been colossally bad in FA or at the trade deadline, at least not during the time period you're talking about.
You yourself said that if you can't get a guy like Suter, you should get a mid level guy. Which he went out and did, in White and Quincey. He later got Dekeyser to play in that role too. He also signed depth defensemen in Colaiacovo, Commodore, and Zidlicky as well.
On top of that he signed or traded for four top six forwards (Alfredsson, Legwand, Weiss, and Cole). Two of them were busts because of injury. We don't make the playoffs without the other two. During that time he also signed depth forward in Tootoo and Sammy. And he brought in Brunner, I don't really know what you'd call him, though he really didn't play bad for us.
Finally, he brought in a backup goalie for cheap, who acted as a bridge between Howard and Mrazek and did a pretty good job...especially a year ago when Jimmy was injured.
So, in the last five years, Holland brought in:
That's not terrible. And, aside from injuries (which you can't anticipate before they happen), it's actually a pretty good mix of players that filled a variety of roles for us.
It should also be noted that we didn't give up a hell of a lot to get any of those guys either. So he managed to do all that AND not mortage the future. I'd say that's pretty good considering the alternative (give up a fortune for guys like Vanek, Iginla, Jagr, Pominville, Nash, Suter, Parise, etc.) hasn't exactly yielded positive returns for the teams who have gone that route.
Wow bold statement!
I love his game right now. When I saw him take the face off with 12 seconds left I just thought of Draper in his prime. Just a guy you can count on to work hard and D the * up.
I was so impressed with Glendening's work ethic tonight. He never made it easy for Tampa and for him to get that game winning goal is just the icing on the cake. He's really become an incredibly important part of this young Red Wings team.
Wings win 11-10.
Third line gets half the goals and Andy gets a hatty.
Mrazek sets an odd record where he never let in a single goal. All 10 of TB goals were own goals by the Wings during delayed penalties.