I think you're really overthinking this. Yes he expected the team to be better, most people did. To be fair, that was true for quite a while.
There's a lot more reasons to trade expiring assets than simply becoming a worse team. We were essentially paid to take Ceci and Walman, and Granlund was traded for cap reasons in the Karlsson trade. Those 3 assets alone returned 2 1st round picks. Grier would have been stupid to decline those trades. That's simply a GM accepting some offers he couldn't refuse.
The Blackwood trade, again was acquired for nothing. Over his 1.5 seasons here he became a legit NHL starter. Blackwood, another expiring deal, was never seen as the starter of the future, and Grier again capitalized on a chance to turn him into more assets. Say what you want about not liking Kovalenko, but I bet our pro scouts believed he could become something just like Zetterlund did when he was traded here. Not every trade is a clear win, sometimes you're just trying to push an expiring asset into an asset you can improve/flip the next year. Maybe they thought Georgiev could be flipped too, idk but at the end of the day they needed a body to finish the year. I'd much rather Georgiev gets lit up every night as opposed to Askarov...who also would behind this defence.
Finally, the Zetterlund trade. I agree this one surprised me, and I thought Zetterlund could be a guy on our 2nd RW moving forward, or someone who just provides some secondary scoring where ever in the lineup. It sounds like management viewed Zetterlund as a 3rd line/middle six player, and with the cap going up, I bet Zetterlund's camp made an offer that caught Grier off guard. As mentioned in this thread or another I can't remember, Zetterlund isn't getting the opportunity he had here on most other teams. Ostapchuk might not be anything special, but he fits that nasty player Grier values. We'll have to wait and see what Zetterlund signs for and what Ostapchuk and the 2nd become.