Step 2 Timing

It shouldn't hinder you too much, but given the chance to do it over I'd take it in July and rotate through November.

You will thank yourself if you take it sooner (same with CS!). The old wisdom of taking it later if your step 1 score is high still works for some people. However, there are many programs that like to see your scores prior to offering interviews (i.e. it's "suggested") and a few that require seeing your CK score to rank you. Given that things are getting more and more competitive each year, our advisor strongly recommended we take it before subI season.

Took CS mid-October, took CK first week of November right before interviews started. I did not feel it hindered me in getting invites in anyway. Also, getting my score midway through interview season gave me a reason to send post-interview updates to programs with some love thrown in.