Genuinely curious - What's the most you're willing to spend on your MacBook Pro, and how many years do you expect to keep it?
I'd go up to $4k for a maxed out unit with AppleCare. Cause I like round numbers, I'd go $5k if I can get it with a new TB display. I expect it to last me until the next redesign or until AppleCare expires (which ever is longer).