Looking at it as individual draft picks or prospects is the wrong approach. “Oh it’s just a 3rd rounder, what are the odds he hits?”. But the value is in the potential because if you get enough of them then you will start to hit. And young players with low cap hits and control have a ton of value. Teams get into trouble when they start paying too much to keep players that are good but aren’t difference makers. If you have a deep pool because you keep drafting a lot then it’s much easier to let players go when they price themselves out and you can replace them from within. It also gives you the potential of finding a difference maker in the rough which you likely won’t through trading the picks for established players.
That’s not to say you shouldn’t trade picks, but I think it’s problematic when you’re at a point that you’re constantly trading picks just to fill holes, because I think you’re already behind the eight ball at that point and unless your core is one of the best in the league you’re not likely to dramatically improve. If you’re keeping lots of picks and restocking the cupboards regularly you can also try to make a big splash for a difference maker if someone becomes available.
That’s not to say you shouldn’t trade picks, but I think it’s problematic when you’re at a point that you’re constantly trading picks just to fill holes, because I think you’re already behind the eight ball at that point and unless your core is one of the best in the league you’re not likely to dramatically improve. If you’re keeping lots of picks and restocking the cupboards regularly you can also try to make a big splash for a difference maker if someone becomes available.