Where you find the best price will, in part, depend on which iPhone you are buying. You may find some deals on the 5s or 5c. It also depends on who your carrier is. Too many unknowns to really provide much help.
As far as insurance goes, I recommend getting AppleCare. Apple provides amazing customer service and it is worth it in my opinion. That is coming from someone who under any other circumstance would advise against buying a warranty so that says something for how I feel about Apple's service.