Casio ctx700 is inexpensive (relatively) and would be a better tool for piano. Sorry to give you an answer that is a purchase, any workaround will probably be unsatisfactory when trying to use Keystep to play piano sounds. That is mostly because while Keystep and Digitakt together WILL chromatically modulate pitch, it will be the pitch of a single sample and will not sound at all organic as the piano sound that you enjoy and are trying to achieve does.
You could load many samples of individual notes, which would give you a slightly more organic sound, but you would then be back to programming notes into the sequencer which is the same as how you stated you didn’t feel comfortable with, which is why you got the keystep involved. Also, a piano has a dynamic attack due to the hammer hitting the strings and use of the pedals, and you won’t be able to replicate that using a Digitakt.
Midi loopback is feeding the midi out signal back into the machine via the din “midi in” in order to address polyphony, and that would have some of the same issues as with the monophonic chromatic manipulation of a single sample. It would allow chords to be formed, but would still sound like a single sample being used to play a chord using a modulated pitch to control the notes.
Using a Retrokits Rk-002 cable you can do some interesting things with midi loopback, but I think a cheap rompler, even a secondhand piano rompler, will ultimately make you much happier. It will perform much more like a piano and in some cases will be a midi controller in itself so you may be able to substitute that for the Keystep while recording. You could also consider sampling that into the Digitakt as chords or riffs and then using those new sampled sounds on tracks, then control the Digitakt with your Keystep as the end game.
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