Duration plays a big part I think. I could easily live frugally if I'm on a one year sabatical. We're shooting for an open ended cruise of very long duration. In order to make that work, I think we'll need more than the basics. A bit more comfort but more importantly a bit of space to stretch out in, gain a bit more privacy and more storage for toys, hobbies, books, DVD's or whatever 'stuff' makes the time pass. I'm looking forward to some good fishing. That takes a bit of gear plus a good sized dink/motor. Need a bigger boat for carrying that.
I'm not purely a 'sailor' but rather a boater who enjoys sailing as PART of the experience.
But that's just me, takes all kinds, eh?