Does Order Really Matter?

Now that I’ve decided that I definitely want to max out my Roth IRA, I’m debating what order I should pay it out.  Should I pay the minimums on my loans and put as much as possible into the IRA until it’s maxed out (probably sometime in July) then reallocate the money from the IRA designation to my loan?  My other option would be to spread the $5,500 over either 12 months (payment of $458/month).

I don’t know if the interest accrued on the loan would be balanced out by the growth of my IRA in that early 2014 time frame.  I would need to know exactly what I’m invested in and how my portfolio would do in that time.

Honestly, I think it’s six of one, half a dozen of the other in this situation.  Do you have any advice?  Do you max out as quickly as possible or try to spread it over a longer time period?