I can see what you are saying, but, you should always grab the best player. It seems like one amazing superstar a McDavid is better to build around then 2 Evander Kanes or a Kane and a Pelech.
Especially since most of the offers I see being offered is a last 1st.
A player drafted late in the first round will usually turn into a 3rd liner or bust. So, a 3rd liner + for getting the less talented player doesn't seem worth it to me.
If you can get a player like Dickenson like you have been suggesting then yeah it could be worth it.