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I feel like there's no such thing as a "sure thing" in round 5, but the skill level difference between consistently good and consistently poor drafters is how often those late round players work out for them. I think the best thing a player can do to improve in their drafting is to be thorough examining the deep part of the class and pay extra attention to the late round guy a dominant player is picking. Hell even ask them why they picked that guy and what they liked about them, you might learn something.
Those guys also stay good by picking and choosing the right guys to keep on their roster, and trading the right guys to increase their draft ammo which gives them more flexibility to trade up and back in drafts to zone in on the specific players they want.
Being able to spot the difference between a player who won't last 2 more picks and a guy who will probably be there in 10 picks is pretty important
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