My ground is very sandy and doesn't support standing water. I didn't need to block them up, they drained fine. I used 100 (5 – gal) pots last season with 4 (3/8") holes through the bottoms. You could easily go with more if you wanted to, it wouldn't hurt. If you're using the right mix for your region it should retain enough moisture suitable for your climate and not over/under saturate your peppers.
You may want to check out this post:
http://www.thehotpepper.com/topic/10245-all-about-soil-a-great-resource-i-thought-i-would-share/