As a generalist, you've not only got my goat, you just took it to town and got it drunk.
This sort of over reasoning is part of what bugs me about this industry.
Many devs change jobs at the drop of a hat, turnover is already high. Yet here you are, worried about job retention, trying to second guess what a dev knows about their own happiness.
I know you mean well, both for the org, and the person, but what makes you think you know, better than the dev, what will stress them out or not?
You aren't them, so just ask, and as long as it is clear they have thought of it, and want to move ahead, you should 100% drop the matter.
Frankly (as if I could be more frank, heh), likely there will be something entirely unrelated which will bug the dev. And all your concerns will be for naught.
Except, of course, you are throwing people's resumes in the trash bin, thus reducing your talent pool, due to unfounded concerns.
