I made the same move from DT to OT two weeks ago. If you read Merlin’s guide (takes like two hours) then you’ll quickly understand some of the conceptual differences, and from then on you’ll be able to get started and get things done. To me it didn’t really feel like such a big jump, as the sequencer works more or less the same (ok, trig conditions are in a weird place, but hey, whatever). The big advantage however is that, from that moment on, the OT has a mountain of features and possibilities still to be discovered, where the DT pretty much is what it is, as soon as you figure it out.
To me it feels like a much more capable workstation for working dawless than the DT. And the crossfader is easy to work with and will be very handy for live play. Not to mention, if you’re setup is small you won’t need a separate mixer. And it does looping. And slicing. And can playback longer samples straight from the CF-card. And it’s stereo. And it’s much easier to backup your projects (not unimportant!). I’ll stop here, I don’t wanna sound like I’m advertising the thing
I haven’t tried the arrangement mode yet cause I don’t plan to use it (I rather record live-performances). But in that area a DAW is obviously much more flexible.