I agree with both the need to bust budget when you're on the cusp of a WS, and the need to continually spend for the future.
If one thing characterized the Giles/Montgomery years, it was a complete lack of vision and organizational philosophy other than "don't rock the boat."
But I don't agree that you bust budget just to spend money, you do it strategically, when you'll get the most benefit.
Right now, the best strategy is to do what they did last year, spend $60M on short-term deals, they got about 5 WAR and 6 prospects, and could have done better with better execution.
Resigning Hellickson, like Morton the year before, was a good gamble, he was worse than expected but still garnered some value in July. Neshak and Benoit were good gambles. So was Kendricks.
Saunders and Buchholtz were overpays ex ante, and disasters ex post. Buchholtz had a bad injury history and Saunders simply had to pound the ball to have any value (negative defense).
Unless you can get Darvish or Lynn on a reasonable 3 year deal, I'd rinse and repeat last year's strategy, just execute it better.
Neither is going to move the needle, so you settle for a 1-2 WAR player on a flippable deal instead of a 3 WAR player who may flame out in a couple seasons on a 5 year deal.
As far as big money deals, to me the only big contracts you should ever give is to your own player covering the prime of his career, that is, something like Kershaw, from age 27 to 32 or so, if you are faced with a Cabrera or Pujols situation, and they want big money into their late 30s, trade them early and move on. You sign your own because you have much better information about their true value.
On the other hand, given organizational depth, there is no excuse not to trade for a couple million in LA allocations each year, I'd offer guys like Martin, Perkins, Pujols, Appel, etc. in a heartbeat, and even guys like Viza, Cumana, Stephen, etc.
And I'd certainly use money to "sweeten" trades they're gonna to have to make the next couple years, buy some A ball prospects you don't have to protect by throwing in a million or taking a bad contract back for real value.