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

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.