Agreed with your entire post, but this part. Willie was coming off a 20 goal/60 point season, almost identical to his 2nd season and at the time I believe the thinking was he should be getting low/mid 6s on a longer-term deal, or at least the just-shy of $7M he signed for was on the high side.
It also didn't help that his father's influence on his contract wasn't encouraging:
"In his 16 NHL seasons, Michael Nylander played for seven teams, including a second go-round with the Washington Capitals. The common thread running through
every stop was contentious contract negotiations. "
One consistent signal beaming from the Nylander camp since contract negotiations started last summer is that the restricted free agent’s father is the one calling the shots
www.theglobeandmail.com
And so there was some fear that "junior" would play hard ball just like his dad did, and look what happened. Dubas went way above and beyond the call to get him signed - way more than any GM should have to for a player that was not the franchise player, or even a star.
So that's why I pointed out that between Timo and Nylander, even if Willie is considered the better talent, Timo is a big, skilled forward the Leafs could use in their top 6 and will likely be the easier negotiation and possibly at a cheaper cap hit. that's if he wants to stay.