Detroit had to do a full rebuild and maybe some of the decisions Yzerman has made aren't the best. But there has never been a GM that has a flawless track record for every decision they make, and there have been other circumstances affecting their draft picks like never improving their position and who is actually available in those drafts by the time they get to the podium. You can have a top 5 pick in a weak draft that's less valuable than a top 15 pick in a deep draft.
Tampa was built from the back end out. They got Hedman and Vasy early on, then added Sergachev and McDonagh by trades made possible by good draft capital acquired along the way. Of course getting guys like Kucherov, Point, and Cirelli with 2nd/3rd picks were essential as well, and they did have Stamkos and Killorn before all this, but they do say defense wins championships for a reason. No they don't win without Point and Kucherov, but they weren't winning without Vasy and Hedman either.
Yzerman has taken 2 studs so far on the blue line with Seider and Edvinsson, then added Cossa in the hopes he can be their #1G for a decade. The first round forwards they acquired will be very good soon, Raymond is already, but the key will be how good the back end is 2-3 years from now. If they get the slightest bit of luck in the next few drafts where a surprise star falls to them, or one of their post first rounders becomes special, they'll be a really good team.
I did not agree with the signings made in the last 2 years, but I can see the rationale behind them. You can't throw out all your youth and allow them to get beaten down with few experienced NHLers to help soften the blows. I think the quantity of guys he acquired was the biggest problem; it's ok to have a few contracts that are not ideal value for money, however they added like a half dozen veterans who are underperforming. Again, it was another product of circumstance where they felt the playoffs were achievable and decided to acquire stability, but getting bottom half in the lineup players through free agency is EXPENSIVE and with older guys there's a far greater risk of a significant drop off in production.
It looks like shit right now because things aren't going to plan. How many times have we seen a team be absolutely dismissed because of a shit season or 2, but then boom they pop off and are competitors? Detroit will have those not so great contracts off the books in no time, and it's a hockey town that can attract free agents better than other division rivals like Ottawa and Buffalo.
He's not doing a shit job but if you're not winning, everything you do will be heavily scrutinized and this is a really bad stretch right now. Should they get a couple of high impact forwards in the next 2 drafts, and manage to make a few quality free agent signings or trades to fill out the roster, they'll be good. And it's also entirely possible that they don't get any luck over the next few years and continue being a bubble team.
These are the perils of being an NHL GM - you can make the best decisions at the time in the moment, but factors out of your control can torpedo those choices in a hurry. Or you can be absolutely incompetent, but have good luck that covers your miscues and misfortune i.e Pierre Dorian. Ottawa has been just as unfortunate In the draft lottery, but the Karlsson trade and subsequent collapse of the Sharks followed by a lottery win got them Stützle. Which also required 2 other teams passing on him. They finished 2nd last in 2018, dropped to 4th but lucked into Tkachuk being available. If San Jose does not move up in the lottery and Montreal picks Tkachuk, Ottawa might have been rocking Zadina and maybe Holtz or Quinn in place of those guys instead. If that happened, the Senators would be in a Buffalo state of being right now. Maybe Andlauer doesn't buy the team or Ullmark refuses to be traded here because the team will not contend anytime soon.
You could say that Yzerman has been frustrated hitting a few posts in a tight game, whereas Dorian took a few shots that were going to miss by a foot, but scored anyway after a deflection off the other teams D's butt.