Not a bad overall list relative to each other.
In my mind, they should get a demerit on every trade that wasn't an expiring contract because, at least from the outside looking in, they didn't need to make those trades. Your trade partners in those trades are doing so because they have an immediate need. In these circumstances, you should be shooting to receive a premium above what the on-paper value would suggest - you should have the leverage. In practice, that's not going to happen with every trade. But Gleeman made a good point that there wasn't one single trade that you can look at and say "Wow, the Twins got great value there" relative to on-paper value. If you're making nine trades, you should be able to say that about at least one of them, right?
And the Outman trade should be an F minus. If he needs to be "working on things" at AAA at the age of 28, then he should probably be playing overseas or in independent ball. I honestly would've preferred a complex league flier in return for Stewart