This was discussed here:
http://forum.game-labs.net/index.php?/topic/862-tacking-sequence/?p=47160
0 is north on the compass, 90 is east, 180 is south and 270 is west. This could be amended to show N,E,S,W respectively with the intermediate cardinal points, NNE, NE, ENE, etc. I was able to deduce it pretty quickly given my line of work where we work with meets and bounds and north is always 0 degrees.
As to the wind direction, I see no harm on simply moving it to the opposite side, it will still point int he same direction but it may be harder to deduce the wind direction with the relation to the yards this way as you try to manually control them. I've found the current set up helpful in this regard. It's a minor issue to be honest and one which is not that difficult to adjust to.
Other games have already done that which NA is doing as can be seen from this video from Age of Pirates: