What you're describing are GMs that wait for the opportunity to find value. People here are currently complaining about missing out on the big fish coming off of the board.
It's rare for rentals to pay great dividends. Particularly at high cost.
Another example of why it's important to maintain a strong farm system is being shown in the Nick Paul trade. Mathieu Joseph, who has developed into a reasonably solid fourth liner was just moved for one of the better power forwards on the deadline market.
And for the record, Mathieu Joseph is ass.
The problem is if you're a bad GM you never find the right oppurtunity to get value. Every summer, every trade deadline, every in-season trading opp becomes a massive struggle.
Which is basically the Oilers in a nutshell.
Long gone are the days of the 1990s when Sather was a top GM and could find player after player after player after player of good young finds that came in and played their ass off for the team, even with shitty drafting the Oilers of the late 90s were an exciting, talented team and even when other teams poached our talent we kept finding other good young players via trade or signing.
Holland is probably going to have a lot of trouble next summer too. No reason to believe he'll do well with the Oilers cap problems, this was the last year he'll have Puljujarvi and Yamamoto and Nurse this cheap and he'll probably not be able to find another Evander Kane to drop out of the sky and he will still have a massive hole in net.