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Okay, I know it's "average" not median ... so it's not exactly half that are overpaid.
But, I think it is important to remember that the $/WAR figure *IS* an average - NOT a ceiling.
I think that is where "some" of the friction comes from. Not that WAR itself should be adhered to dogmatically ... but that the $ per WAR figure is often treated as if it is a maximum.
When do you overpay for WAR?
About half the time.
Mostly, you actually overpay (versus the $ / WAR paradigm), in cases where you are competing with other bidders. This is one of the reasons why many of the underpaid players are underpaid --- they sign contracts in situations where no bidding is going on. That includes the obvious re-sign the guy currently on the roster BEFORE he becomes a FA (home town discount), but also applies to the discard pile where owners are sifting through retreads and reclamation projects (Bay ... Ibanez ... etc).
If you can overpay "a little" in a non-bidding situation, and land your guy, that could easily be preferable to overpaying a lot in a bidding situation - or (as has been the case most often in Seattle), losing the opportunity to overpay - and being stuck with no other option except to scrounge the discard pile. In too many cases, the reality is not - pay for the 4.0 WAR guy and settle for the 3.0 WAR guy. The reality is overpay for the 4.0 WAR guy (at 7.0 WAR prices) ... or pay for the 0.5 WAR guy that is actually available.