I completely agree with your first paragraph. It really does sting to see the Dodgers and Betts having so much success. I'm almost at the point where I'd pull for the Yankees over the Dodgers, but nah. Can't do that.
The odd thing is, I'm really happy for most of the individual Dodgers players. I was very happy that Kershaw, one of my long-time favorite non Red Sox players, retired on such a high note. It's the organizational philosophy that I'm vehemently opposed to.
As far at the Red Sox seemingly not having much urgency, I think it's just their unwillingness to give out the huge contracts. I can't say that I blame them. I think that Henry would balk at the huge contracts regardless, but I think you're absolutely right that the possible lockout is one more additional factor to that.