While it's winter, I was thinking about combining a small digital anemometer / wind direction meter with a gps (speed, heading) bluetooth module and use a PDA with data logging software (like Labview) to combine these values. This way you may just be able to train with a single boat and possibly determine optimal settings for upwind sailing (upwind VMG, corrected for windspeed)

only problem, where can I find a small, but strong and cheap
anemometer? and where to mount this on a f18 (probably masthead?). Has anyone tried this before, or is my thinking too complicated and should I just go sailing... (don't forget, it's winter here <img src="http://www.catsailor.com/forums/images/graemlins/wink.gif" alt="" />)

Thanks!