Son #1 recently picked up a new 'long-term phone', and his strategy is worth repeating:
1) He looked for cheap iPhones (previous year's model) with BROKEN GLASS - we live near a repair place that will replace the glass & battery for $50. He didn't end up getting an iPhone this way, but he found some interesting <$200 deals.
2) He reached out via Social Media, housemates, and workmates - through this, he was *given* a previous-year-model LG phone - FREE. He said, "If I didn't like it, I would sell it on CraigsList."
He felt constrained with the $10 pre-paid Airvoice plan I had him on, so he expanded it to a $30/mth unlimited calling/1GB data plan.