I'm just trying to figure out the best route to take here. If I upgrade early, I pay $28 a month for 24 months. What would I be looking at, cost wise, if I wait until May when my original contract is up?
Usually with early upgrade, if you are offered this, you are also agreeing to give up your current phone. So you lose any future trade in value or other use of that phone. In May, the monthly price for any phone you get is always the current retail price divided by 24 months. So very likely the cost will be the same or cheaper per month for the same phone in May. May sure you clearly know the fine print.