I agree with your basic argument here and you've convinced me to some extent. I wanted to dredge up some examples to highlight inherent flaws in Python's error handling ergonomics, but I was pleasantly surprised by new language features that made the experience much more enjoyable (the with ... as keywords, in particular).

I will say this though: try/except still sucks, in my opinion. I much prefer languages whose standard libraries utilize monads/callbacks for error handling, because it offloads much of the work/documentation onto the type system, as opposed to languages/frameworks which prefer error handling as part of a try/catch statement.

Monad Example (Scala documentation - Try monad [1] ):

  import scala.util.{Try, Success, Failure}

  def divide: Try[Int] = {
    val dividend = Try(Console.readLine("Enter an Int that you'd like to divide:\n").toInt)
    val divisor = Try(Console.readLine("Enter an Int that you'd like to divide by:\n").toInt)
    val problem = dividend.flatMap(x => divisor.map(y => x/y))
    problem match {
      case Success(v) =>
        println("Result of " + dividend.get + "/"+ divisor.get +" is: " + v)
        Success(v)
      case Failure(e) =>
        println("You must've divided by zero or entered something that's not an Int. Try again!")
        println("Info from the exception: " + e.getMessage)
        divide
    }
  }

  fs.readFile('/etc/passwd', (err, data) => {
    if (err) throw err;
    console.log(data);
  });