In the end, even if I go back to Heroku, I'll have gone from Heroku -> VPS -> Heroku. But it's not full-circle or back-pedaling like it first appears. Rather, I've traded Heroku as a blissful crutch for Heroku as an automator of things I now know how to do.
The pain just means you're ready to reach the next abstraction because you've beat the level and paid your dues.