Re: Making a play for 2nd overall (helps or hurts me?)
I think that's too much. Kaprizov and Fox are playing in the NHL next year and they're both good young players, Byfield will most likely be in the minors next season. When are you planning to compete? Keep an eye on your window and stick to that plan, don't get distracted with the draft otherwise you'll always be rebuilding.
Are they in a rebuild too? I'd offer one player and one pick and then negotiate from there depending on what they're looking for. You may want to shop Kaprizov and Fox to other teams to see what you get and then create a new package for the 2nd overall.
League 1
Keep 16 - 4 rookies max 162 GP
Forwards: Point, Tavares, Svechnikov, Boeser, R Strome, Teravainen, Tarasenko, Arvidsson, Tolvanen
Defencemen: Boqvist, Hamilton, Dahlin, Klingberg, Ekblad, Hronek, Marino, Brannstrom, Shattenkirk
Goalies: Vasilevsky, Shesterkin,
Minors: Kravtsov, Tolvanen, Brannstrom
League 2
Keep 18 - 4 rookies max 162 GP
Forwards: J Hughes, Kakko, Cozens, Frost, Kubalik, M Tkachuk, Vrana, A Svechnikov, Virtanen, Buchnevich, Gurianov, Tarasenko, Lehkonen
Defencemen: R Andersson, Jokiharju, Trouba, Valimaki, Cholowski, Leddy, Montour
Goalies: Saros, Sorokin, Talbot
Minors: Heponiemi, Krebs, Tippett, Hoglander, Liljegren, Bouchard,