I don't think you will ever see the Sox go past even 1st Luxury Tax penalty again, as long as Henry owns the team. I think he will get more involved in spending after this season. The current Luxury Tax threshold is $206,000,000.
You should be able to put a WS contender on the field without coming close to that threshold. Right now we are $228,700,637.
The Cubs are next 219,125,039. 2,625.008 over the Cap. Lucky they play in a weak division. Only 2 games up in 1st place.
Funny pattern here, one present Sox GM, and 1 former 1 with highest payrolls.