From a user/developer perspective, we've created a command line utility (`cask-repair`) to make version bumps as painless as possible. Would love to see more people using it [0], and we welcome suggestions and PRs (we have a few long-standing issues that have gone unaddressed, and fresh eyes are always good!)
[0] https://github.com/caskroom/homebrew-cask/blob/master/CONTRI...