My suggestion is to require gems in the Ruby file where they are needed.
If you need a global gem, I would use config/initializers/awesome_print.rb, in which you can add a require "awesome_print", so it would be loaded at the boot time.
Going with Bundler.require(:default, Hanami.env) is for me, as it will slow down your app boot, including each time you start a CLI command or when you reload your code in dev mode.
Thanks @alassek and @jodosha for the answers. I’ve been following Hanami for years and I’ve also tried to keep up with the developments in Hanami 2. But now it’s the 1st time I can really try Hanami 2. Thank you for all the hard work. Hanami 2 is a massive milestone.