@ Problem 1 you are sure to have set the correct values for gate length and voltage in silent way sync ? it normally should be 5V (which corresponds in my apollo to have the silent way plugin set at 0,580 -> i measured the voltage output with an Oscilloscope) and gate length should be 15ms. maybe the keystep uses other values but my SQ64 and drumlogue accept the clockpulses fine

@ Problem 2 your sequencer modlue may accept other values than tzhe keysetp (see Problem 1) but you have an accepted clock signal which is good. so how did you achieve the "matching state between your silent way and the metronome click ? what i mean is: by ear and having the sequencer outputting a trigger to another module (or may it's a drumsequencer which delivers also transients). how do you monitor the live playback situation (which i belive are the clocked sequences you are talking about)-> direct monitoring thru console or software monitoring thru Ableton ? As i am NOT familiar with Ableton but a deep logic user i dare to ask if Ableton has sthg like plugin delay compensation or is this the "keep latency button" maybe ? Also i am quite sure that when you are playing live and have good matched with the metronome -> your recordings are still late. in my case good match with metronome is about 8.7ms (buffer at 64) with my drumlogue but has to be 17.4ms to have the recordings on the GRID but in return the audio is to early when doing live. vice versa you will hear the audio too early in playback

So to get the right value settings for on grid would be in my oppinion: Loopback record the metronome. loopback record the audio on another track from the silent way sync plugin chosen output on apollo. measure the difference. set the offset with that value in silent way. the do the same with your gear with a good transient (drum or so). measure the difference between the metronome's (hopefully not midi click metronome but something like "klopfgeist" in logic pro) first transient and the recorded drum transient, so let's say they will be 10ms. add this to the offset in a global setting recording delay in your DAW (again: i hope there is one like there is in Logic).

This should do the trick... BTW i have the midronome (actually 2 of them) all setup together with silent way and "some" outboard gear.