Pro: skeg
For slow-speed maneuvering, especially in reverse, the spade rudder has much to commend it. It reacts fast and 'with authority', as my dad would say. For sailing (when the actual underbody of the boat is doing the leading and propelling), the two-plane 'bent' aspect of a rudder hung on a skeg behaves more tamely, creating its own Bernoulli effect and encouraging a curved path (like having steerable back wheels on a car, or like all-wheel pivoting on a railroad car). By the same token a single-plane skeg-hung rudder can be very skittery if allowed to get a little too far out of bounds (wear an athletic supporter if you have a tiller!). And Rousmaniere, Stephens, Chichester and others have commented on the almost unbearable awkwardness of a spade rudder in strong following seas or generally rugged weather.
Also (and speaking as one who just recently repaired one, post-Sandy), the skeg-hung rudder is much stronger and provides some sacrificial or defensive material (the skeg) in the event of surfing through an inlet and whacking the rudder on God-knows-what under there. I actually substantially stiffened my spade rudder's rudder post sleeve inside the lazarette and added a short bulkhead damming off that space from the rest of the bilge, in the (however unlikely but entirely possible) event of the rudder shaft's ripping aft into the hull skin. As it is now, I have at least a fighting chance if I hit the rudder fin on something. It's an old-boat fix I would recommend to anyone cruising where you can't walk ashore or get help in 20 minutes.
In response to Jesse's post, spade rudders are under phenomenal stress-- the whole blade, cantilevered out there, takes 100% of it with no help. The fact that 'most boats have them these days' is because they are cheaper to build (and repair), not 'better' technically or structurally. That's also the reason the rudders (like the whole boats) are lighter in construction as well. When our 1970s Hunters were designed and built, there was at least a mindset that boats were to be used for sailing in deep water in yet-unknown conditions. The Hunters of the 1990s and 2000s were designed and built with (what was assumed to be) a conviction that 'most' people don't sail like that any more, that most sailing is done by the day, between safe anchorages at night, and in predictably mild conditions and with plenty of electronic and mechanical assistance.
I'm only suggesting a technical or theoretical position here. What happens in the 'real world' may be entirely coincidental to what is, technically, compromised logic. Maybe I'm just the Dilbert here (!) but I'd prefer to be a little pessimistic rather than optimistic when it comes to working on people's boats, giving them advice or sailing myself. I get the rep of being 'Doctor Doom' on here; but it's true what I have long said: 'Prudent pessimism is the mark of a responsible skipper.'
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