My phones cost me 50-150$ everytime I want a new one (I can't seem to keep a phone more than 8-12 months, I get bored of them).
Simple.
Get a fancy shmancy phone with a 3 year contract.
After 12 months of enjoyment, put it up on kijiji as "free supercoolphone with contract takeover".
They pay the transfer fee, they deal with the remaining 24 months.
Now you can go get another top-of-the-line fancy phone for 50-150$ on a new 3-year (depending what kind of deals the carriers are offering that week).
And the cycle repeats.
Done this with a couple blackberrys, a couple iphones and now I'm on an Atrix. I can see myself getting rid of it around winter time and I'll get the next high-tech Android then.