This is a super interesting topic and something that I’ve been thinking a lot about lately, so I’ll write some of my thoughts.
I’m a percussionist and obviously with percussions you need to practice timing a lot. However, I have lately leaned more and more towards polytemporal music which has led me to question the need for an absolute quantized grid or synchronized events.
Lately I have started experimenting with playing two unsynced sequencers, for example my Octatrack and Digitakt or my two DFAM’s. And my aim is not (always 
) to create some crazy bonkers jazz but quite enjoyable and groovy, although experimental beats. However working with sequencers leads always to different results than when playing live because everything still happens in a grid (or multiple grids)…
I just finished recording my new album and I decided to record everything without a metronome to keep the flow of time in my songs very natural. The timing is all over the place, tempos speed up and slow down and sometimes there are chaotic rubato sections in the middle of tracks. As a solo performance you wouldn’t notice anything because they are all very natural, but if you tried to add any stepsequenced material to this, you’d be in trouble.
When I started adding other instruments, synths and acoustic strings, first I thought that maybe this won’t work at all, maybe everything is shaking and moving around too much. But I told myself that it doesn’t matter and I think the loose approach to timing made the whole album a lot better. There’s freedom and sense of danger that I couldn’t have achieved with playing everything on grid. Sometimes with electronic music I get bored if there’s not one single sound that is outside the grid. It can sound pixelated and rigid to me. (Sidenote: I love listening to techno, but it’s because its strict repetitiveness is intentional — it allows for subtle change and detail in other aspects of music.)
There’s one track on my new album where I wanted to layer some sample based beats under acoustic instruments and that was tricky, because with drum samples you often have a clear defined attack. If the attack is very clicky and timing is out of grid the music may sound clumsy. In my project I went through the song timeline in small looped sections and adjusted every sample manually to create a natural flow. The result sounds very cool and groovy in its own weird way. In another song I wanted to have a rhythmic loop, but the track wasn’t steady enough so eventually the loop would fall out of rhythm. First I wanted to cut it so that it starts every time perfectly on beat. But then I though fuck it, I’ll just leave it as it is and let it fall out of time intentionally. It worked even better that way.
Yesterday when I was mixing one of my tracks I picked up randomly a card from Oblique Strategies deck and it said: ”Honor thy error as a hidden intention.” I think that’s a very good instruction. When we try to achieve something specific, we often aim for either a conventional aesthetic or some philosophical idea. But sometimes the beauty is found in the chaos, in the uncontrollable. A loose timing may feel sloppy or even a mistake if you’re used to quantized music, but it’s all just conventions. Learn how to embrace the uncomfortable rhythms or how to mask them with other noises, and tight quantization will start to feel like a prison.
Some tips:
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You can get away with a lot of imprecision in timing if there is a strong inner pulse in the track. If everything is unquantized and the track feels like it’s falling apart, try to add one element that is in time. Experiment with different options, like keeping the pulse with bassdrum, hihat, synth sequence etc… Sometimes it is enough to have a steady bass drum and everything else can wander freely around it. Polytempic techno is the shit!
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If you make a beat and the timing seems to be off, can you try to mask or highlight the ”awkward” parts with adding a noise layer. For example if the snare is slightly out of time, can you save it with a tiny noise swoosh just before or after it?
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Identify what’s the most important aspect of the phrase you’re trying to record: if you like the sound, the timing is not that important. If the melody is the most important, the rhythm might not be that crucial. If the rhythm has to be exact, then maybe sequence it or learn to play it like you want it to sound. I think being intentional and consistent in your performance is the most important aspect!
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Time is a concept, we can create beautiful stuff with it! Don’t let the sequencers limit your musical thinking! 
I hope this sparks some thoughts!
I have even done this on OP-1 by recording to the tape, if the timing was too off, lift 12 seconds drop into drum sampler, then resequence with one of the sequencers, repeat for subsequent 12 second chunks. Even easier with OT, kind of cheating but it does work well, depending on material.