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I don't think there is much down side to signing stars to there first big free agent contract, particularly if they didn't sign away their first couple years of free agency.  Alex Rodriguez's was worth the contract he signed with Texas, Barry Bonds was worth the contract he signed with SF in '93, Beltre was worth his contract as well.  So this is the no-brainer category, but it is also rare. Unfortunately, no players of that quality and age profile are available this year and only two were available last year and they cost 7X$23M and 8X$22.5M. 
I grant you Lackey would be worth the numbers you listed, 4X$13M, and I would gladly sign on the dotted line, but such a bargain with a premium talent is also very unusual (the Vlad Guerrero contract comes to mind).
I think the key to the situation for the M's is that they need to figure out how to best use their resources, to maximize their market advantage against the A's and Indians of the world, without bidding head-to-head with the Yankees. This means not necessarily holding out for the Teixieras of the world since that involves direct bidding against the Yankees, though you can always know there roster holes ahead of time and find cases where they aren't going to bid.
If I'm Jack and I'm sitting on a lot of money this year as well as a lot of roster uncertainty, I make short term commitments with big money up front to improve the short term without costing me longer term flexibility.  I don't want to give Lackey 5X$16M, but would be go for 3X$21M?  If he's as good as he thinks he is, he'll more than make-up the difference with the next contract, but the M's avoid the albatross contract.  Isn't that the way to do stars and scrubs without having your star turn into Chan-Ho Park?