I've talked about this before on here, but there's no good reason to have auto-save switched off. Whenever you talk to people about why they do have it switched off, they (mostly) have one of two reasons, both of which are based on a misapprehension:
1/ I don't want recording / playback interrupted by a save
This doesn't happen. Sonar will never auto save during recording or playback, no matter what the auto-save settings.
Interestingly, though, you can manually save during playback, and I've never had that cause any issues.
2/ I don't want Auto-Save to overwrite my project.
It doesn't. It creates a new file called "auto-save of xxxxxxxx.cwp". And you can generally ignore these files unless you need to recover after a crash.
There is a third reason not to use auto-save which is a good one. On very complex projects, the save can get slow enough to be a bit of an interruption to working. But if you're not having that problem, there's no other reason not to have it switched on.
So I think in answer to the OP's question: "Will Sonar/Windows EVER develop a way to be able to retrieve a project when this happens?", I'd say Sonar has developed a way, and it's Auto-Save. It's not perfect, but on the other hand, I haven't lost more than five minutes' work in literally years. I think it's almost a decade since this was last an issue for me.