Couple points to make (but not that I'm necessarily disagreeing with you):
1. I don't have a problem with us resigning Rust and Rakell to their deals nor trading for Smith. In a vacuum, each of them are solid top 6 wings when they are performing. Rakell hit 60pts last year including 28 goals. We need that. What we don't need in 3 of 4 top 6 wings underperforming regularly. As we know at this point, likely a coaching issue but it is what it is. At the beginning of the year, Smith was hot. Rust was hot. Rakell wasn't but he is now that he's back. What we need out them is consistency. We know they are all capable of more.
2. We have to go for late 20's, early 30's guys for a couple of reasons: A. They are RFAs until 27/28. From 18 to 27, they are usually good value wings to the teams that have them and thus are not available or they have a heavy price tag that we can't afford (and shouldn't be affording). B. It takes awhile to perform at the level that makes them a good candidate for a trade - like Rakell. C. You only get the young guys you draft. 2 of 4 are draftees for us - Jake and Rust. We benefited greatly from high-value contracts from them for years. Rust at $5mil is still a good value. Smith had what he had but it's not like $5mil is outrageous for him. Rakell you can question but looking at comparables, he got the going rate. None of these guys are obvious misses like a Jack Johnson or Rob Scuderi.
3. They seem to all have similar skill sets but at the same time, it's hard to find top 6 quality wings with different skill sets. There aren't many Patty Hornys or Matt Tkachuks out there that can provide that valuable skill set that's not what you see from who we have. Those players are highly coveted unless you want to take a chance on a guy like Armia or Greenway.
What would really help us is another Sheary, meaning a guy we pluck from the NCAA for free that provides a top 6 wing skillset and chemistry. Ideally, someone "like" ZAR but that has the impact of what Sheary did.