The other side of the coin is if you buy a newer, somewhat better performing CPU now, it's probably going to last quite a while. Especially if you're not compelled to upgrade your CPU every year or two, you'll get a lot out of it, even if it costs a little more up front.
If we're talking about buying new, the gap between Haswell Refresh i5 and Skylake i5 isn't huge right now (maybe $25?). Like Shivoa mentioned, Intel probably isn't going to have a huge price drop to clear out their older CPUs. More likely to find individual vendors offering good deals every now and then, while Intel offers incremental price drops over time.
Start checking PCPartPicker, if you aren't already. Maybe check out /r/buildapcsales.
If you're building to a certain budget, and the money saved on a previous-gen CPU gets you into a better GPU than you'd otherwise afford, by all means go for it. Socket 1150 boards and DDR3 are still popular, still widely available. If you have some budget flexibility, consider the current-gen options.
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