Wait 8-10 years. Some internet browsing and a good night's sleep will seem an awesome Friday night.
Some commentary on your post:
I'd do the Montreal deal, but I'd rather try to package the two for a better defenseman and forego the forward addition.
I'd probably do the Green deal, contingent on the defenseman returned for Brouwer and Johansson.
Not a fan of the Orlov for Killorn deal at all. Orlov's a keeper, and Killorn offers nothing more than a Brouwer or Laich.
Nay on dumping Laich. He's a very useful player when healthy (and has looked it recently), and cap space isn't an issue at all.
Yay on Erskine, Grabo, Fayne deals.
Nay on Iginla term. I'd rather throw a very high salary at him for 1 season ($6.5-$7M), as cap space, again, isn't an issue.
Probably a nay on Weaver. I think someone really strong on the boards needs to be paired with Schmidt/Orlov, and Weaver looks like he's lost a step or two this season.
PK Subban intrigues me. I assumed that the shopping of him on the trade board was typical Montreal fan reactionary stuff, but if there's any legitimacy to him being shipped, I'd dangle a big package (Green + Brouwer + Johansson + Orlov/Schmidt) for him. I really want on impact acquisition on the defense.
The Eller and Laich parts are pretty contingent on Laich's play for the rest of the season. He's looking better, and if he stays healthy I'd be fine with him at 3C, but that remains to be seen. If he looks good, I'd try something around Brouwer and Johansson for Edler instead. Part of the reason I liked Eller was because he's had a terrible PDO this year so he'd be a great buy-low candidate, but the same can be said for Edler.
I think Killorn could easily reach Laich's peak, maybe even surpass it. He on pace for 19-26-45 in his second season, which is better than what Brouwer and Laich are doing right now. Adding the 2nd was probably unnecessary though.
It occurs to me now that Iginla for 3 years blocks Wilson's development unless Ovie moves back to LW when Oates is gone. One or two years is probably better.
Subban would be amazing, but it's hard to believe they'd be dumb enough to trade him, and further to trade him for a package. I think Carlson would have to be involved for them to listen.
Edit: The "Return of Laich" version
Brooks Laich ($4.500m) / Mikhail Grabovski ($5.000m) / Alex Ovechkin ($9.538m)
Evgeny Kuznetsov ($0.900m) / Nicklas Backstrom ($6.700m) / Jarome Iginla ($6.000m)
Jason Chimera ($2.000m) / Marcel Goc ($2.000m) / Joel Ward ($3.000m)
Eric Fehr ($1.500m) / Michael Latta ($0.900m) / Chris Brown ($0.853m)
Jay Beagle ($0.900m) /
Karl Alzner ($2.800m) / John Carlson ($3.967m)
Alexander Edler ($5.000m) / Mark Fayne ($3.500m)
Mark Fraser ($1.500m) / Dmitry Orlov ($2.000m)
Jack Hillen ($0.700m) /
Braden Holtby ($1.850m)
Philipp Grubauer ($0.579m)
CAP SPACE (22-man roster): $5,412,650