Ok, so in regards to my cutting of samples, I've figured it out now.
Due to some sloppy file management from my end, I've loaded multiple versions of the same sample from the +Drive into the project. As in three version of "Andy's Awesome Loop."
Now, the Digitakt don't like this at all. As soon as I call on any other version of the file than the first one I loaded, it cuts it in half.
It's kind of a user error. But it's kind of not. Why shouldn't I be able to use multiple versions of the same file, once it's in the project? And if I can't - which I'd be prepared to accept - then stop me from hurting myself, goddamit.
Anyway, good thing is, all my spectacular recordings are intact, so I'm off to the mine again to do some serious work.
EDIT: I also unloaded all duplicate samples from the project, to avoid further confusion. Apart from the fact that I could unleash this on myself without the Digitakt stopping me, the Samples and Sounds system makes more sense now. Obviously, I should've called for a Sound file as I continue to develop the track, and not keep diving into the +Drive and just load sample after sample, like there was no tomorrow.