Some news in the past 5 months:

Crystal is now %100 funded for a full-time developer working on core - https://twitter.com/CrystalLanguage/status/98229223882167500...

Crystal Automated Release towards 1.0 - https://crystal-lang.org/2018/03/09/crystal-automated-releas...

A summary of why vs. why not - https://medium.com/@DuroSoft/why-crystal-is-the-most-promisi...

Web Frameworks Status:

Rails inspired (with Influence from Phoenix):

Amber - https://github.com/amberframework/amber

Lucky - https://github.com/luckyframework/lucky

Both look healthy in terms of community and updates but Amber seems to have a slight edge.

Sinatra inspired:

Kemal - https://github.com/kemalcr/kemal