Dadonov - $4MM in
Puljujarvi - $1.175MM out
Jones - $850K out

Your trade increases Edmonton’s cap hit by $1.975MM

I don’t mind trading Dadonov, as I believe he should be on a win now type team, and not on a win in a year or two team, but Ottawa isn’t retaining for that long. He’s already on a very team friendly contract anyway, so the cap issue needs to be addressed in a different way.

Including Caleb Jones helps the value, but Ottawa can’t take a defender without giving one back, so Wolanin needs to be in the deal, and if Jones is removed, different value would need to be added. Chiasson makes the most sense to add, @ $2.15MM and an expiring contract.

Puljujarvi - $1.175MM
Jones - $850K
Chiasson - $2.15MM
$4.175MM out
Dadonov - $5MM
Wolanin - $900K
$5.9MM in
$1.725MM increased cap hit, or $250K less increase than your trade scenario.

Why would the Oilers do this, nothing against Dadonov but there could be way better top 6 winger options out there. Why trade JP when he’s still trying to find he’s niche here, he’s getting better and better.

I kind of feel like this is one where the value might not be far off, but I don't think either team would do it.
Trading Dadonov with retention 1 year into 3year UFA signing isn't going to help attract free agents to Ottawa.
Puljujarvi has come back and improving, Edmonton probably wants to reap the benefits of the pain they've taken in development.

Why such a bad goalie? Why Brian Elliot?

Oilers go .500 and give up 5-6 goals a game

Elliot is better than Smith IMO - look at their stats comparatively over the last three years for proof. I’m not thrilled with Elliot, but he was all I could afford after stacking the top 6 with all-star talent.

Who are the better options?

How’s that? The defence is mostly the same personnel as this year, and if anything is stronger defensively with Murray in and Barrie out. Nash is strong defensively. Hall and Dadonov aren’t great defensively, admittedly, but are unlikely to give up that many goals as you suggest.

Because I was exaggerating

So we’re talking this off season, there can be openings on players like Laine depending on if it’s a short stint in CBJ and that experiment doesn’t work, he’s expiring this year. At the trade deadline the Oilers could look at Rakell, Debrusk as of right now, on what could be available.
Why not go for someone like Schwartz who would be free on free agency day, a lot more options out there tbh and some that’ll be opening up when teams figure out if they’ll compete for a playoff spot or not. Having 3 offensively dynamic players won’t work unless they have chemistry as well. We need a power-forward or a defensive forward that brings an offensive ability, I think Holloway is the perfect guy for McDavid but we won’t see him for at least another 2 years. If we’re looking for a scoring forward this offseason I doubt it’s Dadonov.

Smith has a .985% and 0.50 GAA rn... and I'd say Craig Anderson, Cory Shcneider, etc. are all better than Elliot