IIRC, Holland was pretty much making the picks while he was Director of Amateur Scouting and Assistant GM, so you can probably lump Osgood in there too. But that's still two goalies in almost 30 years of drafting.
IMO, Holland just has really strange luck with goalies, and often times it works out the exact opposite of expectations:
-Expectation: Now that Vernon is gone, this guy Hodson will be a great back up
Result: In less than a year Hodson loses the #2 job to Norm Maracle
-Expectation: Bill Ranford will be great insurance if Osgood gets hurt in the playoffs and then we'd like to re-sign him in the offseason when we lose Maracle in the expansion draft
Result: Ranford dumps the bed hard against the Avs, forcing Osgood to play hurt
-Expectation: Hasek is going to return and be backed up by Legace, and we'll trade Joseph.
Result: Hasek is unspectacular in the rare instances that he's healthy, Legace starts for most of the back half of the season and then Joseph finishes in the playoffs.
-Expectation: Osgood is coming back to be starter and will be backed up by Legace.
Result: Osgood gets hurt, Legace never loses the starting job and then craps the bed in the playoffs.
-Expectation: Osgood just won us a Cup, so he'll be the starter and Conklin will be back up
Result: Conklin carries the team into the playoffs while Osgood is a dumpster fire
-Expecation: Osgood almost won us another Cup, so hopefully he can start again, because we have absolutely zero cap space to re-sign Conklin. Also because of the cap and because he might be lost on waivers, we have literally no choice but to make Howard the back up.
Result: Howard quickly steals the #1 job and ends up 2nd in Calder votes
-Expectation: Even though he was pretty bad with the Blues, we think Conklin can have another good year in Detroit as Howards back up.
Result: Conklin is garbage and Joey MacDonald comes in to keep the record home win streak alive and steals the back up job.
-Expectation: Yeah, I know we said Joey MacDonald rightfully earned the #2 job for next season, but we couldn't pass up the opportunity to sign Jonas Gustavsson. We think he can push Howard and challenge for the starting job in a contract year.
Result: Gustavsson starts that first season on IR, and never gets going once healthy, forcing the team to ride Howard. Howard ends up posting a near career year and almost gets the team to the WCF, helping earn him his much maligned current contract. Outside of a decent couple of months, Gustavsson spends around 2/3's of his tenure in Detroit on IR and is otherwise utterly forgettable when healthy. Meanwhile, MacDonald gets claimed on waivers by a basement Flames team that loses Kiprusoff long term and actually plays surprisingly well in locking down the starting job in Kiprusoffs absence.
-Expectation: With his 6 year deal, Howard will be a good starter for the foreseeable future.
Result: Howard struggles with injuries and poor play in the first 3 seasons of the deal. He then loses the starting job for a while, and is mired in trade speculation before gaining the job back because of...... (see next expectation)
-Expectation: We see Petr Mrazek as the starter going forward and will try to address the situation with Howard to fully hand over the team
Result: Mrazek dumps the bed hard, gets unprotected in the expansion draft and eventually traded to the Flyers where he still remained a complete dumpster fire
This is why I said earlier in the thread that they'd probably be better off just giving someone like Hammond $750k instead of paying good money or assets to get a goalie with higher expectations like Hutton or Grubauer/etc.