Earlier quoted context omitted.
Asking because I feel this way a lot too -- is this the kind of thing that was avoidable (IE if you built it on Rails/Django + Heroku would that have cut down the maintenance), or was there intrinsic complexity to the project that made it unavoidable? More and more, I want to build things that are in the former category if I build them at all outside of work.
Depends on what you're building. Rails/django/heroku are web app accelerators. If you are building a web app, then yea they make it super easy and take away a lot of having to think about complex systems, but if you're building anything else not really
The way I'd describe it is that /most/ codebases can fit into what you'd call a "web app" including most codebases that include complex systems -- there are, of course, significant exceptions.