North winds are the most common and desirable at East Shore. The wind tends to be clean, and if you get in trouble, the worst that can happen is that you end up in Stewart Park.
However, you should make all effort not to stray below the docks; not only does it become harder to self-rescue, but you'll also get in the way of other boaters.
NOTE that the schematic above assumes the wind is due north. Usually the winds will be NNW-NW, in which case the dotted lines should be slanted appropriately, but the landmarks remain the same.
South winds can be deceptive because the water is flat, and a very windy day can look windless to the untrained eyes.
There is also no safety net on a south wind day -- if you get in trouble, you could drift four miles before you reach Myers!
Therefore, everyone, especially beginners, should be extra conservative. Pay heed to these landmarks:
South winds tend to be gusty. This makes it more challenging to sail, but is a great opportunity to learn to read the ripples on the water to gauge the wind strength (a useful skill for any sailor).
If you get caught in overpowering conditions, drop your rig and take a rest; chances are good that before long there will be a lull in which you can recover. But to take advantage of this you need to be able to read the lulls in the ripples.
West winds are swirley and flukey. Since they're on-shore, we aren't too concerned about beginners getting in trouble, as long as you stay between the houses to the north and the docks to the south.
If you stray further, however, the thing to keep in mind is that winds may shift, and an unfavorable shift from a west wind could easily leave you far downwind.
The best defense is to check the forecast to see which way the system is expected to shift (more often than not the winds will veer clockwise, towards a north wind).
We don't get east winds unless it's a Noreaster, in which case you should not be out sailing!