I wonder how much of Web Objects will end up in this attempt.
Hopefully, the answer is largely none.
WebObjects was absolutely amazing in its day for one primary reason: it made it possible to write web applications statefully. Instead of having to think of a web application as a series of distinct pages, each of which had to reimplement a bunch of the same underlying logic (remember, this is in an era where /foo/bar/baz generally referred to a Perl script named baz in the /foo/bar directory), you could instead store all the application state server-side and basically write a web application as if it were a desktop application.
There is one thing in WebObjects that I would arguably like to see in Swift, and that’s EOF. But on OS X, I’ve largely got it via CoreData, and I’m not sure that a Swift-native solution would honestly look that close to EOF in any case.
I may be jaded, because of the peculiarities of the particular (enormous, eldritch, non-Euclidean) WebObjects system I worked on, but I would run in horror from EOF in particular, as it never ceased to amaze with terrible, unpredicatable performance; lack of thread-safety; and disastrous, no-good, very-bad Active Record affordances.
In a merciful universe, the answer is none.