There is actually no set law to answer any of these questions besides that you get 90 nonconsecutive days in Schengen as an American. If you are thinking to leave to Turkey for 4 days when your counter hits 86 days in Schengen, expecting to clear your stays (like many people assume), and you come back to Schengen, the counter starts right back up from 86 days. You have to be out of Schengen for 3 months in an 180 day period before you are cleared of your 90 days in.
As for being penalized: You can get the full 1200 euro fine for overstaying by one day. It depends on the officer, the country, what you look like, how you act...hence me saying just play dumb and oblivious in my previous comment.
However, if you want to hear of countries that could be more relaxed on this subject, this would not be a 'legal' answer, because those with the knowledge of that, have already done an 'illegal' thing by overstaying. And I guess I cannot give these answers according to experience on stack exchange!