going all-in does not produce any guarantees...there is this strange misconception that shortening the window while modestly increasing the odds in a particular year increases your chances of a championship...
i think the smarter approach is 1) to focus relentlessly on value, 2) be realistic at the deadline (sell some years, plug weaknesses the years you are in contention), 3) avoid the risks associated with long-term deals that pay 30 something players big money...there is no magic bullet out there, but these common sense rules will increase any team's chances of success