No, they wouldn't do that trade.

Win now would mean keeping hoffman

Hoffman is better than Simmonds by a huge margin. Hoffman is turning 27, he's in his prime. Boucher was brought to keep hoffman

Better yes by a huge margin, no.
This trade, remember, is done with the assumption that Ottawa cannot come to terms with Hoffman

Hoffman is better than Simmonds and it's not close at all, he had 29 goals with horrible coaching. He was placed on the fourth line a lot, he wasn't placed on the first pp unit for most of the season, and he hit 9 posts at half the season, which was the most from any player in the league, and i don't know how many posts he had at the end. Anyways, with a proper coaching staff this season, he'll get atleast 40 goals, and could get 50 if he plays all 82 games, he's that good

And Ottawa is coming to terms with Hoffman, and if they do trade him, they'd do it at the trade deadline

Well then, i guess all is good in Ottawa.
I do think you underestimate the value of Simmonds. And to blame coaching on why a player hasn't performed up to expectations is one sided. The coach and organization probably knows Hoffman better than you so if he wasnt on the 1st line power play and if he played on the 4th line, why do you think that was? And how many post does every player hit during the course of the season? Thats the player hitting the post not the coaching.
And if he isnt playing all 82 games who's fault is that? You are making me think that maybe I over spent on Hoffman.

Hoffman is much better than Simmonds by a large margin. Simmonds produces at a high level, but his numbers are highly ballooned by his power play totals. In terms of production and possession, Hoffman is the far superior player. I don't think it would be a wise trade from Ottawa's perspective.

I think you are 100% correct, as far as it being a wise trade, not on Hoffman being far superior. But again I was basing this trade on the assumption that Ottawa couldn't come to terms with Hoffman and if Philly presented this deal I think Ottawa takes it because: 1) Simmonds can score 2) Simmonds is a leader, physically and mentally 3) Simmonds contract is probably the worse contract a player at his level has and 4) you are receiving a much coveted 2nd round pick.

If the Flyers keep Schenn they dont/cant make this move.

haha what else, Simmonds is also the best player on the NHL? no thanks, if Simmonds is soo good, why not keep him, I mean he is a thirty goal scorer right? Ottawa has enough "leaders" now. They'd probably accept this horrible trade though if Simmonds was an Ottawa native and if you guys paid them his entire contract, but thankfully, Simmonds isn't from Ottawa. Simmonds is a minus player that is good at tipping in goals and beinnifitting from giroux and voracek. He is not elite like Hoffman. Perhaps Ottawa would accept giving Hoffman up within their division if an outstanding trade like giroux, who is an Ottawa native, for Hoffman is proposed. But I don't see that happening anytime soon, so enjoy Simmonds.