To me, in an ideal fantasy world - which would never happen - VAN is better off giving up assets in the meantime to clear up space so we actually have room to make additions while this core of EP, Horvat, Boeser and Hughes are in their primes.
Trade Pearson for maybe a mid-round pick, force Baertschi and Sutter in the top 6 to try and pump up their numbers. Since they both have a year left they may be movable with salary retention. Benn could probably be moved at the deadline for a late pick.
From earlier in this thread it was mentioned that the Wings might be looking at taking Demko + Eriksson for SJS's 3rd rounder. Considering it took a 1st round pick to move 1 year of Marleau, that would actually be somewhat palatable...
Sign a goalie in UFA to back up Marky, perhaps Domingue?
Re-sign:
Markstrom - 6.25M x 4 years
Domingue - 1.2M
Stecher - 2.5M
Virtanen - 2.5M
Gaudette - 2M
Leivo - 1.75M
MacEwen - 975k
This scenario for 2020-21 already acknowledges that there'll be some short-term pain given our cap situation, but aims to improve our situation for the future. So yeah it'll be ugly, but necessary. One step back, two steps forward...
2020-21:
Miller - Pettersson - Sutter
Baertschi - Horvat - Boeser
Leivo - Gaudette - Virtanen
Roussel - Beagle - MacEwen
Edler - Stecher
Hughes - Myers
Benn - Rafferty
Markstrom
Domingue
Bear in mind there's just over 10M left which could be used on Toffoli or Tanev depending on how you view those 2 in terms of asset management.