Use Ruby 2.X, no more ruby-debug
Update dates
RSpec 2.99 with helpful deprecation warnings
Inventory transpec
Convert specs to RSpec 2.99.1 syntax with Transpec

This conversion is done by Transpec 2.3.3 with the following command:
    transpec

* 9 conversions
    from: it { should ... }
      to: it { is_expected.to ... }

* 4 conversions
    from: its(:attr) { }
      to: describe '#attr' do subject { super().attr }; it { } end

* 1 conversion
    from: == expected
      to: eq(expected)

* 1 conversion
    from: it { should have(n).items }
      to: it 'has n items' do expect(subject.items.size).to eq(n) end

For more details: https://github.com/yujinakayama/transpec#supported-conversions
Looks like transpec missed two things
Inventory RSpec 3!
Fix deprecated custom matcher syntax
Clean up some whitespace
Recreate spec_helper, add dotfile with $ rspec --init
Include our lib and spec support files in spec helper
Remove comments from spec helper
Ignore .rspec-local