Current quicken doesn't run on Linux, and the web version doesn't connect to any online investment accounts as far as I know, only bank accounts.

Ableton would still have the issue of: which plugins can I still somehow get to work? And which do I just lose? And then: how reliable is it? Does it really just work, or am I gonna be fighting glitches all the time?

I suspect part of the problem might be a mental block on my end. I spent 25 years as a sysadmin before I retired, and the idea of going back to that is just not acceptable. And I know it would be hundreds of hours because that's what I spent last time I tried to make the switch a few months ago.

I know it’s not the same application but Quicken Simplifi definitely connects to investment accounts.

Hundreds of hours makes me wonder what distribution you chose…I think if you choose something that’s more designed to work out of the box as a ready to go solution you might have a better experience. For example, since I like occasionally playing games, I chose Bazzite which comes with all the gaming stuff installed already and is an immutable OS that “just works.”

And for sure, I think trying to shoehorn complicated non-Linux applications into your Linux workflow might waste your time. I tried this with Autodesk Fusion and I almost got it to work. But it didn’t work. So I just use that on Windows, but it’s also nice to not be bothering with Windows for the majority of what I do.

The way I do it is that my laptop is Linux and my desktop is on Windows and I can just RDP into it over WireGuard to use Windows apps. So I guess this is cheating: ideally my desktop also leaves Windows but I haven’t made that leap.