Two options here, if you buy a phone on contract for say $200, then you can always sell it in a year, or even two, for around double of what you paid for it. Example, iPhone 5's are going for around $450 in my local market. I just paid $200 a year ago for it on contract. Some people hate contracts and say it's cheaper to not have data or what have you, but like I said this is just this particular scenario if you are on a plan.
Option B, you can buy a device for full price, ie $650 and wait the year or two and sell it for ~$450 but now you have a gap of $200, but you still own the device outright. Sometimes depending on what carrier, you can get an iPhone discount of $100 when not in your contract and that could bring it down to ~$550.
These examples exclude taxes and exclude some abnormalities with the pricing and buying markets such as unlocked > locked phones such as Verizon. Verizon phones don't have the same desire as AT&T phones because of the CDMA vs GSM difference with being able to use it on other prepaid carriers easily and worldwide use.
Anyway, that's my two sense from what I've learned over the years. If you buy a phone on contract and take care of it, you'll still get a great phone and double your money in a year when you go to sell it. That's how the markets have been treating them so far over the years.
Edit: I will say that if you wait too long such as the large jump from 4 to 5S, the resale value on the 4 is now dipped to ~150-200. So to me it makes more sense buying every release or two on contract, and then letting the phone pay for itself.
Getting a new phone as part of a 'subsidised' contract is effectively borrowing money to buy a phone. Your loan repayments are the monthly fee. If you have the cash, buying the phone up-front is almost always cheaper.
BYOD means $20 off your monthly bill (or subsidizing is +$20, whichever way you look at it), and the BYOD rate is legitimately substantially cheaper than similar plans from AT&T or Verizon.
Plus even if you subsidize the device the terms are far better. The $20/month goes towards paying off a debt, which is simply unsubsidized price - subsidized price. If you leave early you pay the remaining balance and the phone's yours. This is in stark contrast to AT&T's rather punitive early-termination fees that exceed the actual subsidization provided initially.
It's absolutely cheaper to buy devices outright here.
Example of Three's One Plan for a 32GB 5s (£):
24 mo contract
Device 99
Plan 46
24 mo total = 1203
12 month contract + BYOD
Device 629
Plan 15
24 mo total = 989I also can't believe I can just connect to the internet from anywhere, and there are not even any tubes connected to my phone. How is that possible?
1) 10 years ago this was way bulkier, far less convenient and more often than not without an intertube connection,
2) 20 years ago this was absolute bare-bones and only for upper middle class and rich people,
3) 30 years ago it was science fiction.
Now, a 20-something would of course take all this for granted. But technology will have some surprises for him down the road too, and he'll learn to put things in perspective when 2030 tech is 100 times more awesome than today's.
Technology always seems to progress both faster and slower than you think.
The 5s has been my first new iPhone since I got an iPhone 4 in 2010 and for me, coming from an older device that didn't even have Siri, I am extremely happy with it. It may be a moot update if you already haven an iPhone 5 (or maybe even a 4s) but to me it feels like an entirely different device (not only because I also updated to iOS7 at the same time, of course).
I really like the finger sensor, as it makes login a lot faster. Of course, there're security issues here, but for me it is just a convenience method, if people are able to break through this sensor, they will also be able to use other methods to gain access to my data. I also look forward to apps that leverage the M7 as I tend to do a fair bit of walking and running and like to see at the end of the day how well I performed. I really like Siri, again, this is my first time having access to it, and I already use it for writing text messages, checking the weather, or creating schedules / appointments. In general, the speed difference between my old iPhone 4 and this one is staggering. This, of course, was to be expected, as the 4 was crazy slow at times, but it still makes me happy.
All in all, for me, the 5s is a great update and I hope that the 'most forward thinking phone yet' comment from Apple is close to the truth, as I again, plan to use it for at least 3-4 years before updating again.