I think the argument regarding the market's perception of Smith and what they would pay for him ignores what the Penguins would be looking to do here. Based on pretty much every trade deadline, Smith would bring back a 3rd or 4th as a rental next year and possibly even a 2nd if he has a good year. What's really the benefit for them to pay to move him in the off-season, when waiting 9 months likely gives them a much better return? They're not a win-now team anymore. A team might say "you'll have to pay us to move his deal", but the Penguins can rightfully say "we can just hold onto him and sell him at the deadline for value".
I might see them being willing to trade Smith for nothing to just get his contract off the books, but if any trade is worse than that, why wouldn't they just hold onto him until the deadline? Even if he just repeats what he did last year, trading him at the deadline with 50% retained likely brings back a 3rd round pick (either straight up 3rd or 4th that can turn into a 3rd). That's exactly what happened with Kuznetsov, Tarasenko and Roslovic last year, and prices were abnormally low last year as well.
In a world where Chad Ruhwedel brings back a 4th as a rental, I don't really see a reason to pay to move Smith in the off-season if you can just wait until the deadline to move him.