If you can hold out till spring there will probably be a swap meet with other boardheads cleaning out their garage for the umpteeth time trying to get rid of boards they havnt used in years- check out Toronto windsurfing club for possible dates.
People are more stoked to see their old gear being used by someone young and enthusiastic like you than sitting in their garage for another season.
Im sure you can pick up a decent board a few years old for $300 or less.
Dont think about it as money lost but invested.
You can always sell the gear later for at least 1/2 that.
+ you get better on a newer gear!