You need 25k points to get grand reserve. When you buy "winery direct" bottles from TW (they have them marked) you get 10 times the points when those coupons are active. So basically you can buy $250 worth of wine to get the necessary 25k points. I usually do it in smaller quantities since we don't drink wine very often. I'll get about $75 worth (6 bottles) every 4-5 months.
Edit: you get 10 points per dollar spent. So you are getting 100 points per dollar spent with the coupon active.
Edit: you get 10 points per dollar spent. So you are getting 100 points per dollar spent with the coupon active.