But you don't need analogies to understand why ASI is a bad idea. ASI means that when you leave out a semi-colon you get unexpected behavior instead of a syntax error. Failure is always better than the unknown. At least then there's a chance the bug will be found and fixed.
ASI is supposed to work in exceptional scenarios where you would have ended up making a mistake but wouldn't want to be reminded of. And that is supposed to be in rare scenarios.
Now if you make exception the norm and expect tools to make up for bad practices then its not going to help.
And this is why I think Python's forced indentation is in some way bad. Because it makes the code from a bad and good programmer both look same. And merely forcing code indentation won't magically transmogrify a bad programmer to a good programmer. There are many things to good programming and indentation is just one of them. Worse it will make both's code look the same.
Forgiving or masking or making bad practices look good doesn't help on the longer run. It only encourages such behavior. I am sure bad programmers can slip in easily into these communities than else where, because they are difficult to flush out and their mistakes are often forgiven or made look good.
Proceeds to offer an even worse analogy. Good one :)