One thing at a time:
1- There were thoughts that Lehkonen could possibly be a second line winger. Didn't turn out that way, but still, he was drafted on potential.
Speaking of Chiarot, are we talking about the same Ben Chiarot that we signed as a free agent and didn't use any draft picks on? Just making sure.
2- I could go a decade of swings & misses in the second round. But you know what? If in that one year out of ten, I get Sebastien Aho, or Nikita Kucherov? I've got a fucking badass player for the next decade, too.
3- As mentioned over & over, if I want players for my third pairing, or my third or fourth line, I can get them Every. Single. Summer. I could ever get them via trade for peanuts if a team is strapped for cash. Derek Ryan's going to be available in a month, he'll cost us $1M over one year. Reliable, safe, fourth line winger and I won't need to waste a 2nd round pick to get him.
4- If I'm really, really desperate for a player that is in demand for contending teams, I'll just trade for one and give up a second round pick. I'll have a player that's established in the NHL, I know exactly what he's good at and there won't be any projections required, or having to wait 3-4+ years to see if he can actually make the NHL. While I think Beck might even make it on the roster next training camp (I thought he looked more NHL ready than Slafkovsky did last Fall), there's no guarantee he sticks once he's here.
I'm surprised you of all people will take this position.