A hole is not a stress riser. A notch is. Looking at Mainsail's chainplate, the maximum strength of the part is at the minimum cross sectional area of the steel on either side of the hole if the pull is straight up. Some back of the envelope calculations assuming a 3/8" wide by 1/4" section times 2 (the sections on each side of the hole) would yield a total breaking force required of 13,875 pounds. If the hole were only 3/8" in diameter then the total breaking force would increase to 16,188 pounds total tensile force. The reduction in strength is approximately 14%. This also assumes 74,000 psi tensile strength for 304 stainless. If this is still within the load requirements of the boat with an appropriate safety margin, then it is probably ok for a chainplate with this much meat on it. Thicker on all sides of the hole would be better.
Allan