Misery loves company!
Part of my problem has been that I've read way too much Joe Sheehan on Twitter, who has a very anti-owner sentiment. While I was never the biggest Jerry fan in general, it has led me to question how limited team's resources truly are, and in turn more pessimism about the chances of Sox signing a Machado or Harper.
As a small business owner myself, I fully understand that a business needs to be profitable, however I don't think major sports franchises should be looked at the same as other businesses. Your #1 goal should be to fill your trophy case with championships. And the owners aren't depending on the teams to make a living, they are already very wealthy individuals from other lines of work.