I file late almost every year. Once I filed for 5 years in one day. That time I owed a shitload of money but they were really quite nice about it and set up an easy payment plan. They waived all kinds of penalties and shit just for the asking and were really helpful about the whole process. They really don't get too worked up about late filing, just don't cheat.
Now state income taxes, that is another story. Those pricks are brutal to deal with so try to keep a low profile with them. Almost went to jail over that.
