IRS Publication 560 2009 on page 2 says that a Simple IRA can be rolled over to become a Roth IRA in 2010. IRS Publication 590 2009 page 71 contains the statement "However, you cannot convert any amount distributed from the SIMPLE IRA during the 2-year period beginning on the date you first participated in any SIMPLE IRA plan maintained by your employer."
Employee X first participates in the Simple IRA plan on 12/30/2008 with final participation on 12/31/2009, and no participation in 2010.
Question 1: Can Employee X convert the entire Simple IRA contributions made starting from 12/30/2008 on 12/30/2010?
Question 2: Is Employee X restricted from converting this Simple IRA plan on any day in 2010 prior to 12/30/2010?
Assuming the answer to question 1 is yes, then tactically how can this be done in a limited two day window? I suppose the Roth IRA can be created without a contribution at some early point in 2010, which gives some target account into which the conversion funds will be placed. But is there some specific form number that the broker must then file, whose exact date must say 12/30/2010? Or is the requirement that the actual funds be deposited on 12/30/2010?