Green(50% retained) to a Cup/playoff contender. Return-Mid to late 2018 1st.
Nyquist(50% retained-signed thru 18/19 so not a pure rental). Return(with retention)mid to late 2018 1st or 2 2nds(18/19).
Howard(50% retained-signed thru 18/19 so not a pure rental). Both the Isles and the Hawks could/should/will have serious interest in Howard given the shaky tender situations of both teams. The Isles have the leagues' worst GAA and the save% aint much better. Howard is definitely an upgrade over Halak amd Griess and with 50% retention, very affordable. Return is higher of NYI or Calgary's 2018 1sts. As for Crawford, rumors of his possibly having vertigo, reminds me of Franzen and his concussion history. Crawford could be out a week, a month, the rest of the season or his career could be over. Return-2018 1st or prospect(s).
Booth: Moved for mid to late rd. pick
Can see this happening
To NYI: Green + Nyquist + Howard (all three with 50% retention)
To Detroit: Higher of Calgary/NYI 2018 1st and 2nd rd picks + Halak(cap dump) +Nelson
Given the Hawks, Islanders and Flames respective current positions in the standings, I doubt they offer up those 1sts unless they are lottery protected or have a condition that allows them to defer to sending a 2019 1st if they so choose.
And as far as goalies going to Chi/NYI, it sounds like both teams don't want to spend big assets to get one, given that they don't have a strong hold on a playoff spot. The Islanders in particular seem to be more apt to shore up their blueline instead of the net.
IMO, your trade makes little sense for both the Red Wings or the Islanders.
First off, the Red Wings would be strapping themselves with $5M+ of dead space for 18/19. Not a huge deal by itself, but then you have to consider that they would need to re-sign Nelson as an RFA and sign a goalie to replace Howard, which likely takes up most if not more of the $5M+ they save not having half of Nyquist and Howard on the books.
For the Islanders, Garth Snow would need to find a bomb shelter if he trades futures in that deal and then either A: They miss the playoffs, B: Tavares finds a new home on 7/1, or C: A and B. Especially when you consider that the deal would only impact their team for as far as the end of 18/19. The only silver lining is that they might be able to move Howard and Nyquist at next years TDL for some assets.
I also doubt Howard would have NYI on his list of 10 teams or Nyquist waives his NTC to go to a team with the worst home ice surface in the NHL and a questionable future in regards to their best player.