New Horizons' encounter with Pluto was the first big fly-by mission since Voyager 2. How difficult was it to prepare for a fly-by when every planetary mission since then has been an orbiter? You are correct, there's not been a major fly-by reconnaissance mission since Voyager, but the previous missions that performed fly-bys to each of the planets, from Mercury to Neptune, helped to develop the techniques and we benefitted from that.
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