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G, you saved me from a long post. Said it all, as usual.
I think you're point about Jack Z wasting opportunities when he WAS given the go ahead to spend a little is right on. However, the problem he has faced every time, in my opinion, is being given just enough money to fail, not enough to succeed. He was allowed to stretch a little, but a little further stretching (not a lot) would have opened him up to opportunities that would have had a higher chance of success. As it was, he had to choose among poor options and hope for a break. Now, maybe he's just a lesser GM when it comes to that particular aspect of his job. That's entirely possible. Few are geniuses at EVERYTHING.
But in my opinion the larger issue, the cause behind that problem, is the repeated symptom with Mariners management to go only so far and always stop a buck short of success.