If we keep Simmonds all year and then mutually part, assets be damned, we're still looking at this next year strictly in-house for our bottom 6:
Laughton-Frost-Lindblom
???-Vorobyev-NAK
I cannot imagine both Frost and Misha aren't on the team in 2019-2020 at worst. Misha might already be a full time player this year at some point. That pushes Laughton to wing, or Frost to wing. Lindblom can play both wings. NAK will be waivers eligible, so he'll be up at 4RW perhaps. Lacyznki and Allison hopefully are signed and can be potential mid-season promotions. Someone else in the organization can surprise (Kase?). Another year and you add Farabee and O'Brien perhaps, both capable of playing RW. Ratcliffe will be around the corner too. Not all of those players are RW, but most can play RW or will shift someone over.
I can get saying Simmonds fulfills a role this year. Next year? The reinforcements are there already. Too many actually, which could force a trade sooner than later. You don't totally block them another 4-5 years -- which has a value domino effect down the prospect line -- for similar but cheaper production.