I don't have good advice but we are in a similar situation with DD who just turned 4 about 3 weeks after the cut off date. That means she is scheduled to do transitional kindergarten next year followed by a year of kindergarten starting 3 weeks before her 6th birthday. Currently by my estimate she is moving into early 2nd grade math and reading levels. I don't know whether to do transitional K next year as she is turning 5 then try to skip to 1st or try to enter K next year at least. I hate to have her make friends in TK then skip and lose those friends since social interations would be the only thing she will get out of the year besides getting used to being in school all day every day. I think we will test but we may be able to wait until 4.5 years or so.