facts as I see them
In lite air,if your great,and he screws up,maybe ,but lite wind if lite gusty is going to make bigger boat slow,in higher winds you should take him if as said your boat work is as good as his and take note of; J24's are dry sailed mosty(from the trailer)and your H34 is wet sailed,so your bottom and keel and rudder(prop?) may not be as smooth as his bottom etc.(no prop)& or your sails not as good even if your boat work is,that can hold you way back.Don't take this wrong,but your using a bus to out run a car,thats hard,if you even come close on time get you and your crew some beers.