That much stacking of opening parentheses is never seen, only ))))))).
Typing )))... is easy; just hold down the ) key to repeat, and watch the cursor jump back and forth due to parenthesis-matching. When it flicks back to the correct target, release, and backspace over any overshot parens.
Agreed. Though I'm mostly a scheme and C hacker these days, I did Python professionally for about 13 years, and that is a very nice side effect of the whitespace thing. On the other, Python has no decent equivalent of Lisp's let, and complex or nested Clojures of anonymous functions are butt ugly in Python, so now I'm happy with my parens.
Look crazy to fresh eyes. I've found it to be a non-issue the more I write lisp code. With structural editors like parinfer, paredit, smartparens, etc. it becomes a whole lot better.
Practice quickly gets you past that point. You read Lisp by looking at the indentation. You write Lisp using tools that modify the code structurally, rather than on a character-by-character basis.
((((((((((((((((( by the way