Expecting a short term, high cap hit, contract. something like 3-4 years @ $8.5-$9 million per year cap hit.
Doubtful we'll see that.
He'd be leaving potentially millions on the table.
Let's compare a 7 year, 49M deal vs a 4 year, 34M deal
If we're assume a "standard" salary structure for both (i.e. straight salary, not significant amount in signing bonuses)
The first obvious issue is the 2020 lockout issue. Now, I'm assuming there will be some structural ways to protect from that on both (minimize salary/maximize signing bonus during that year). However, there might be some serious structural changes to how contracts work (basically stopping the 8M SB/ 1M salary style deals) which could cost skinner some long term cash. There is also the potential of the compliance buyout, which have been a boon to the players who have gotten them. Under a longer term deal, Skinner could play 4 years, get the final 3 years CBO'd, then sign at a lower rate someplace else.
It's almost always best for the player to take the most guaranteed total $$ on paper, irregardless of term. Taking a shorter term, higher pay deal could yield more, but is more likely to yield less $ overall as its doubtful he'll another long term deal at the age of 31 or higher.