Wouldn't it have been simpler for them to raise prices for new customers a year ago and leave the existing base grandfathered in?

It seems like I have this discussion at work from time to time. The faster we grow our customer base the harder it is to monetize our improvements, because we have a smaller and smaller pool of new users.

Getting big before you get your feature set and cost structure down means you have to go ask forgiveness from old users.

If instead you launch a big ad campaign after improving functionality and increasing the prices...