You can ask anyone too, no one is more hard on a GM that does a shit job than me, but honestly while Holland hasn't been perfect looking at the Oiler needs exactly 12 months ago
1.) Too slow, plodding of a team, desperately lacking skill past McDavid/Draisiatl.
1 Year Later: Haven't properly integrated Athansiou yet, but still this team is now at least on paper comparable to other young/fast/skilled teams like Toronto now. They are reasonably skilled and can roll several players in 3 on 3 OT now instead of having to play two guys to death.
2.) Getting rid of Lucic for someone who contributes badly needed goals.
1 Year Later: I would say more or less he accomplished this task. Neal isn't perfect, everyone and their grandma would've told us this deal was impossible a year ago. 19 goals from Neal, several coming in 1 goal victories for the Oilers definitely gave the Oilers a 6-7 point cushion in the standings they wouldn't have otherwise, that is a huge difference.
3.) Koskinen Problem - Mikko could look great at times but it was clear he needed a solid 1B goalie to sometimes overtake the 1A spot.
1 Year Later: I would say Mike Smith effectively basically addressed this need. Guy struggled in December but then massively has come on since Jan. 1 with a red hot record.
4.) Horrendous Penalty Kill. Was losing the Oilers games.
1 Year Later: One of the best PKs in the league. I'd say job well done.
I'd say more or less he has addressed virtually all of the major Oiler needs in some fashion with some help in the form of Bear, Yamamoto, but still he has done that without trading a 1st round pick or any significant roster player.
Considering Chiarelli had to trade an immediate 1st round pick (Islanders used on Barzal) and also Taylor Hall to get anything moving here, to only really give up two 2nd round picks as the most expensive piece of the puzzle for what is probably a better overall team than the 16-17 team ... I mean how much really can you complain about that.