Where are you getting a $365 iPhone from?
If you trade in after only one year, you basically paid a dollar a day to rent the phone. But if you had bought one outright and sold it at the end of the year in order to buy the new model, you would not be a whole lot better off -- and you might have had to deal with potentially scummy eBay or Craigslist buyers.
And the cost difference is the same as the cost for Apple Care, which is included. So if you were going to sign up for that (which I have to do) you're already breaking even.
The prices are not bad either. They seem to range from $32.41/month up to around $46/month for the most expensive possible model, which translates to about $1/day up to $1.40/day. It includes AppleCare as well.
I just looked up prices on CL, and it looks like the used-iPhone market is approaching saturation... The going rate for 1-year-old iPhones is 150-200.
eBay probably has a more accurate picture of price for the average person.