Keeping 1st round picks (even late 1sts) is critical to help keep a steady stream of young ELC players that can contribute and keep costs down. A standard 3rd liner or 3rd pair UFA will make around $3 million. By having 2 ELC players on those roles that allows for $4 million to be allocated elsewhere.
If picking in the 1st and 2nd round every year it’s not unreasonable to draft 2 players that can be top 9 FW or top 6 D every 3 years. It’s when teams keep shipping top 60 picks out for expensive roster players roster players.
That would assume that you're hitting on a majority of those late picks (picks in the mid 20's are 50/50 to play 200 NHL games) and that there is a linear development path for them to come in as another guy phases out.
That and then do you deal them as soon as they're proven and due for a raise or do you deal the next guy behind them because you have an NHLer and a bird in hand is better than two in the bush.
Think we will run into that situation with Zetterlund this year. At 25 and on a cheap expiring contract, is it worth the extension into the $4M range for 3-5 years because you know the player and how he fits or is he more valuable to trade and hope that you can find that type of player with the trade assets (probably nets a 1st rounder and more if not 2 1st rounders a la Brandon Hagel in 2022) in a few years time.
I'd steer away from dealing 1st rounders mid season at the TDL because I think the impact you get for that pick is putrid compared to what you get during draft week, but I would make a nice blend of using a pick in the 18-24 range on a player some years and to address an immediate need in others depending on what is available.