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Re:Just-In-Time Static Type Checking for Dynamic Languages by ufo on Tuesday April 19, 2016 @08:26PM (#11531531)
Point #1 would be very very hard to do for Ruby, since its such a highly dynamic language. The University of Maryland team thats behind this paper already tried doing that with Diamondback Ruby but it didn't really work out in the end.

janvitek.github.io/events/PBD13/slides/JeffFoster.pdf

They apparently changed their focus to gathering type information at runtime and using it to do interesting stuff, like this recent Hummingbird research.

By the way, I think it might be possible to implement autocompletion based on that runtime information they collect.

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