Interestingly, I actually first considered the set of 303s + set of 808s route. I know some female pros ride a 303/808 combo at Kona, and given my timidness handling the bike in higher winds in aerobars, I figured maybe the 303/808 would be the better combo. I also figured the 303s would make a nice all-around wheelset for a road bike (of which I have too many).
But prevailing opinion is that you should go as deep as you can with front wheel, as that makes the biggest difference. Also, what I've noticed on my road bike is while there was one a time I felt quite skittish riding my Bora 50s, after plenty of time riding them in all sorts of crazy weather it's very rare that I don't feel comfortable on them (high wind + narrow shoulder with lots of cars or long, technical, gusty descents maybe the only exceptions.). So my theory was go with the 808, train on it a lot and eventually I'll get used to it and dropping down to the 404 would feel very "safe". I think training on the 404s and racing on the 808s when winds are light would work too.
But if I'm missing something, in the 404 vs 303 decision, I'm all ears.
But prevailing opinion is that you should go as deep as you can with front wheel, as that makes the biggest difference. Also, what I've noticed on my road bike is while there was one a time I felt quite skittish riding my Bora 50s, after plenty of time riding them in all sorts of crazy weather it's very rare that I don't feel comfortable on them (high wind + narrow shoulder with lots of cars or long, technical, gusty descents maybe the only exceptions.). So my theory was go with the 808, train on it a lot and eventually I'll get used to it and dropping down to the 404 would feel very "safe". I think training on the 404s and racing on the 808s when winds are light would work too.
But if I'm missing something, in the 404 vs 303 decision, I'm all ears.