In VIM, at the moment when I need to comment out a section of Ruby code:
gc ir (inside Ruby block) and ar (around Ruby block) for Ruby do ... blocks. im/am for inside/around Ruby method, and iM/aM for inside/around Ruby class. gcir / gcar comment inside/around Ruby do/end block. gcim / gcam comment inside/around Ruby method.gciM / gcaM comment inside/around Ruby class.gcc to comment a line, or 5gcc to comment 5 lines.All in all it's very Vim-like and natural.
Hope that helps.