She doesn't have to literally kick herself. I will resolve this according to my best judgment.

Relevant facts: She's a Ruby on Rails developer, CTO of Beeminder, she's not like a Vim guru, just extremely comfortable with it. She's wary of steep learning curves, likes using git from the command line, etc.

UPDATE: This is open-ended and only resolves if/when she fully switches over, at which time I will quiz her on how much she regrets not switching sooner and resolve accordingly.