These are really nice questions / concerns.
- Firstly, we are a Ruby shop and most of the time the errors are pretty self descriptive that we can easily solve. Also the IRC/Gitter room is full of helpful people that you can get instant feedback about any issue (even a compiler bug). Note that we're not afraid of writing code :)
- I've updated our application once in the last 6 months. It's only a minor change for adding type annotations which took like 10 minutes.
- Actually i think that Crystal is already in beta quality (for us). Calling it Alpha is really an understatement.