You're mesmerized by cap hits. The analysis of whether a contract is a "bad" contract involves a three-variable equation: cap hit, actual salary, and performance.

The fact that Benn's cap hit is the third highest of all LWs is utterly irrelevant to the issue of whether it's a good contract or not, as a nanosecond's worth of thought should establish: Connor McDavid has the highest contract of all centers, and David Pastrnak's new contract will be the highest among all RWs. If they perform the way we know they do and will, who cares?

Let's start with some basics, founded on what you yourself have said: Hischier is an excellent player. He is "just as good production-wise" as Benn. He costs more than Benn, despite his cap hit. Hischier is younger than Benn, and will probably become more productive in the future than he is now, while Benn will probably regress with age. Now, what are we to conclude from these accepted facts?

(1) Despite the fact that Hischier plays a more productive position, and plays on the first line and thus gets more playing time on ice than Benn, he isn't outperforming Benn. Now, no one with an ounce of knowledge about hockey would say that Hischier's contract is a "bad" one, so how can you argue that Benn's contract is a bad one?

(2) The fact that a contract may age badly as the player ages doesn't make the contract a "bad" one now; I recall more than just a couple of players named Chelios and Chara that played pretty well into their dotage.

(3) The fact that you, and probably I, would take one player over another is utterly irrelevant as to the issue of whether one player's or the other's is a "bad" contract.

Let's take some examples:

(1) Player A has a cap hit of $8 million and a real salary of $6 million. Player B has a cap hit of $6 million and a real salary of $8 million. They have the same number of points. Who has the "bad" contract?

(2) RW "PK" has scored 50 points in 61 games and has a cap hit of $10.5 million with a real salary of $6.9 million. RW "PL" has scored 48 points in 53 games and has a cap hit of $8.7 million but has a real salary of $9.1 million (i.e., 50% more). Who has the "bad" contract?

Cap hit is merely a fact -- a factor to be considered in the calculus of "good" vs "bad." Production in light of cap hit and actual salary is truth.

1) Hischier is a significantly better and more valuable player than Benn, with a significantly lower cap hit. If benn's cap hit was 7 mill, you'd have a point here, but it's 9.5
2) The fact that a contract is likely to age poorly matters, because the contract still has term on it.
3) Comparing players to their peers matters. A top 20 LW with a top 3 LW cap hit is overpaid, a top 20 C with a top 35 C cap hit is underpaid
4) except for AZ none of these owners are broke. To actual contending teams, Cap hit is massively more important than salary, in a hard cap league.
5) player As contract is worse, and PKs contract is worse.
6) Nico Hischier has a real dollar amount of 4.5 mill this year if that matters so much to you.
7)
Mcdavid is the best player in hockey making the most money. Not overpaid.
Pastrnak is at worst a top 3 RW in hockey, again will not be overpaid (may be by the end of his contract tho)
Jamie Benn is not a top 10 LW. Overpaid

Current Production>Cap Hit>Term>projected Production (based on age)>Real Money

Oh and I didn't even get into the fact that this is one bounceback year for benn at 33 after 4 mediocre ones, propped up by a career high shooting % (18% after shooting 12.5% over the last 6 years) and very unlikely to be sustained.

You're not listening, and you're wedded and welded to your position, so I'll give up now.

Your only position is that "cash means more than anything" "player decline with age isn't real" and a bunch of awful comparisons.

If Jamie Benn hit the market he would not receive a 3 year deal at 9.5 mill AAV.
If nico hischier hit the market today he would receive more than 7.25x5