Firstly, thanks for an honest and non arrogant response. These are hard to come by on this forum some days.
I don't think they should give insulting offers, like they did with Delgado after 2004. I believe team could have done a better job by protecting their image this offseason. They just had their best year in over 2 decades, fans expect them to try and take that next step, especially considering the short-ish term nature of their roster. Shapiro mentioned building a sustainable winner, which is great and all but the team is already very close... it feels like they might be sacrificing a little bit in the short term by not making that one last aggressive move because they are afraid of what might happen to the team in a few years. Their roster is so strong that their marginal wins are more valuable than they are for more teams. Their willingness to pay for an extra win should be very high right now, but it doesn't quite feel like it. The media and fans are always going to want more, but from what I've gathered Shapiro hasn't been well received so far... this is just my perception from talking to people out in the real world (i.e. away from fangraphs).
I think they will have a very good team, but the Red Sox are a bit better IMO (and betting odds as well as projections reflect this). Even if they think they can build a sustainable winner, the Yankees and Red Sox will continue to have 2 of the largest payrolls so I don't think chances like this will continue to come around often. I am not drinking the Kool-Aid and believing that they will contend year in, year out anytime soon.