Upwind speed - what to look for in a boat?

The reality of where I race is that a lot of the events have a significant upwind component – often into some wind chop that really kills the boat run with the hull slamming down on the other side of waves. We hear a lot about what makes a ski fast downwind or on the flat, but I would like to know more about the characteristics that make a boat faster upwind? Are less nose volume, more rocker, and a shorter ski characteristics I should be looking for or am I better off with less rocker smashing through the waves rather than bouncing over them?

From Oscar Chalupsky:

Oscar's input about the rounded hull slapping less is interesting, I have found the opposite.  The boats that slap the most for me have a rounded hull up front- G1 V12 and the original Uno.  The same holds true in the team canoes- the old school OC6's like Bradley Lightning and Mirage have rounded hulls in the bow and they are terrible upwind compared to the unlimited boats with sharper cross sections up front.

The worst upwind boat ever, for me, is my G1 V12, which has a high volume, rounded, wide bow, and low rocker.  The best boats I've tried are the shorter ones- V11 and the Nelos come to mind.  V11 has fair amount of volume in the bow and more than average rocker, Nelo has low volume and minimal rocker.  

It makes sense to optimize upwind if your courses are out and back.  Lets say you bash out for 5 miles, turn a buoy and surf home.  You bash at 5 mph for an hour, then turn and surf at 10mph for 30 min.  I'd rather have the boat optimized for the hour long piece!  But of course it's not all or nothing, I'm sure you can find a good upwind boat that surfs great...

My impression was that when Chalupsky said round would slap less he meant round as in less flat, not less vee. 

Going into steep, short chop I definitely feel like a shorter boat might help. On a 14' standup paddleboard, a pintailed design with a high volume, well-rocked, well-rounded nose goes upwind best because it bobs and pivots over the chop like a rubber duck.  

Since the bumps in my area are short, steep, and disorganized I have often wistfully eyed the V11 / Nelo style of boats while struggling a bit both upwind and downwind with my Stellar SEI G1. 

My V7 is pretty rounded and it loves to slap.
I also feel that when I am out with my sea kayaker friends they seem to have easier time bobbing over the waves in their rockered boats when I partially ram through. My speed is about the same as a run of the mill 17 feet sea kayak in tkihose conditions (which may be simply due to me being inexperienced)

I also spoke to Hein van Rooyen of Carbonology Sport about this and his take was:

• In their experience, shorter boats go faster upwind.
• A sharper V hull reduces slapping, but causes the nose to bury deeper into the oncoming wave, requiring more energy to power through.
• More rocker helps going upwind, but compromises speed...

He said, "in general, stay away from extremes" which is probably good advice!

In summary, in BigFish's circumstances, a shorter boat would probably be an advantage.  

But there's no simple silver bullet answer!

My experience is that I have found that my Think EVO and Fenn XT with a dramatic "V" shape in the hull from the nose to the cockpit perform upwind much better than any other skis with a more rounded hull that I have paddled. My 19' XT paddles surprisingly well with little slapping upwind, you just have to be prepared to get wet!