I know this doesn't address all your concerns, but I switched from Ableton Live to Bitwig Studio for unrelated reasons to my leaving Windows behind, and I was t

I know this doesn't address all your concerns, but I switched from Ableton Live to Bitwig Studio for unrelated reasons to my leaving Windows behind, and I was thoroughly pleased with how easy the transition was between the two DAWs (I guess it shouldn't be too much of a surprise given how many ex-Ableton devs work on Bitwig), and how well the Linux build of Bitwig worked. Bitwig on Linux, with Pipewire as the audio engine for low latency operation, is essentially an identical operating experience for me. Getting your plugins working is a different story. A small but growing number of mainstream audio plugins have native Linux builds available, a wide swath of them work quite well with yabridge (https://yabridge.org/ https://yabridge.org/ - so shim to expose Windows audio plugins running in WINE prefixes to Linux audio plugin hosts), and a few required alternatives to be found. I found the workflow decent enough to use, but as one might expect, some plugins not working well via yabridge/WINE made things a little janky, and once I picked up a Mac device again, that became my production machine. That said, WINE's come a long say since I last tried this out a few years ago, and I'd be interested to see if things work better. My point, I suppose, is to share a reasonably good success story (though perhaps still not of a grade that you'd be comfortable switching to for paid work), and perhaps to encourage you to consider some alternatives to the tools you use. Tool changes are expensive, sure in cost, but moreso in time, so I don't suggest it lightly. That being said, I think that it might be worth it to grab a Bitwig trial and see how you like it. I'd grab it both on Windows and Linux, so you can try it "how it should work" when your plugins and the DAW are working in harmony while also getting the Linux toolchain working. And from the cost perspective, Bitwig does not have crossgrade licenses, so you can buy Studio once, and run it on any supported platform.