I've had to deal with Ruby for the last 2 years, and one of the main problem is the gem ecosystem. The language and standard libraries are pretty narrow, unless you add Rails (which adds a new variety of breaking upgrade headaches).
Thus, there's always the desire to use third-party gems to achieve pretty basic stuff (localization, decent networking/REST, database drivers, etc). These then tend to go out of date. It's pretty common to find well-used gems that haven't been updated in 5, even 10 years. This puts the developer in a tough spot - reinvent the gem/wheel? Or be forced to stay on an EOL version of Ruby?
Thus, there's always the desire to use third-party gems to achieve pretty basic stuff (localization, decent networking/REST, database drivers, etc). These then tend to go out of date. It's pretty common to find well-used gems that haven't been updated in 5, even 10 years. This puts the developer in a tough spot - reinvent the gem/wheel? Or be forced to stay on an EOL version of Ruby?