I haven’t tried the MS at all, so I can’t say where you’re coming from.
I doubt you’ll have any issues with the framework of the Digitakt. You already know the basics from working with the MS(select sound, plug in note, alter parameter here, sound design)
The issue you’re probably concerned with is the sampling element of it- which is the new thing, and the menu-diving element of it. The sampling element of the machine couldn’t be more simple. You do it one time and it will be like you’ve done it a million times- its that intuitive. Absolutely a breeze, one of the key points that anchors the DT so deep in my heart.
The menu-diving might give you a bit of frustration- having all the parameters available at once certainly offers a good degree of convenience. I think it will only matter from a performance perspective. From a sound design perspective, its very straight forward and focused. With the graphical display upgrade from the MS it should make you feel more cerebrally connected to your sound. If you like to live alter parameters of each sound, you might have to practice it a bit more. I don’t do that frequently, so its not really an issue.
OB is also pretty straightforward, once you get working with it. and for your recordings, it records everything you do in a performance- so you can fine tune every element to make the best representation of your track.
Its a great instrument. My favorite thing I’ve played with.