I agree with several of your points. That said Jackson and Ferris worked together for a year under the Orr Group so there is pretty solid familiarity beyond this client negotiation. Jackson is also infused with the same deep personal (and legal) commitment to negotiate the best deal possible for his clients. As such Ferris acted within the parameters of the CBA including common practice to ask around for market interest in his RFA clients. If anything, given the Broberg trade request and Jackson's familiarity with Ferris's aggressive approach to looking after his clients, then important to smoke out those intentions early.
I'm not surprised at all if, as reported, the Oilers delegated the contract negotiation to what sounds like Bill Scott. Jackson's shown his leadership style include trust and delegating to his management team. These are after all younger, secondary players on a Cup contender. If the active negotiation timeline was moved up, there's likely ability to make a hard decision on whether or not re-signing one, both, or neither is likely.
Unfortunately Ferris did his job.
I think the fact the two of them working under the Orr banner for a year is pretty irrelevant, doubtful they worked closely in any capacity as they each represented their own clientele. Also, How do you know that he didn’t “smoke out those intentions” earlier and based on the feedback he received felt confident that they were going to be able to get a deal done?
Knowing what we know about how both Jackson and Ferris operate I find it hard to believe that Jackson would commit such a huge unforced error with his most important young player given the information he had. I find it far more likely that an agent who’s been known for shady negotiation practices would give incomplete or incorrect information because it was to his benefit, and he knew he would always be able to cover himself off down the road by saying “oh sorry my client changed his mind”. To believe that Ferris was upfront with the Oilers during negotiations you have to believe that Broberg sat on a 4.6M offer sheet for weeks waiting for a team he requested a trade from to meet a 1.8M ask, which is less then half of what he had on the table from another team.
End of the day, they should have just traded Broberg because they really never had a shot at signing him barring matching a big risky overpay. But it seems they believed the partnership between team and player was salvageable, sides were within 500k or so and team felt that a fair deal wasn’t far off.
On Holloway I’m sure it caught them off guard that an agent would advise a client of the forwards age and experience to walk away from the opportunity to play on a Cup contender that features two of the most productive talents of the modern era. I’ll never fault a guy for going for the money ever, but that was a mistake, especially right as you’re breaking through and finding some traction with a player like Leon. To me it kind of shows a guy who lacks confidence and doubts himself, and maybe the mangled wrist played a factor in his decision but the kid could have had it all. Ride along for a few cup runs with some generational talents and in a couple years if you held up your end then you’re likely making back that money and more or at the very least signing a Foegele type contract.