For my family of 4 the upgrade price I'm willing to pay is probably more in the $150/night range. As Rookie2008 noted, it's really personal preference.

We take advantage of the breakfast, but I wouldn't value it at $100 if we don't have Napua we usually grab breakfast from the grab and go downstairs, the Starbucks and the Wailea Beach Resort, or the coffee shop in the shops. The drinks at the bar are nice but I wouldn't compare a drink from the bar there that I have to drink near my room to the same price as one down at the pool.