No you wouldn't. See Javascript for all the pain that causes. Language syntax needs to be dictatorial so that the language is consistent for reading (which is more important than writing).
Technically, Python is a much better example of optional semicolons since you can use them and they're not required. Of course, the real reason they exist is for compound statements.
Untrue. While it's true that most people use the 'layout' rule, which is the significant whitespace, there is a non-whitespace-significant variant that uses braces and semicolons. You can see an example of how layout is expanded to the alternative syntax at http://www.haskell.org/onlinereport/lexemes.html#lexemes-lay...
Very few languages consider non-indentation whitespace as significant (not counting using whitespace as a token delimiter, which Haskell definitely does, e.g. "foo bar" =/= "foobar").
For Ruby at least "heavily" is a big exaggeration. It is significant as a token separator and in cases where inserting a line break makes the expression up to the line break a valid expression in itself, in which case it is treated as one.
You pretty much only need to remember to separate tokens where lack of whitespace might create a different vald token, and ensure any expressions that you want to let span more than one line ends with something that expects following tokens to make a complete expression.
Personally I can live with that easily. I can not live with significant indentation, on the other hand...
Yes, but many people assume whitespace everywhere will matter when they hear Python's offside rule described. It's a misconception I've found is worth dispelling, since almost no one minds meaningful indentation.
