We own 4 weeks at OP, 3 silver and 1 plat. My original plan was to use the plat last week in April and one of the silvers 1st week in May and the 2 other silvers in Sep/Oct time frame. Did this for a few years until the points program came out. April/May was a nice visit weather wise but Sep/Oct were really rough surf conditions. I enjoyed it as I grew up on Long Island and the beach conditions were similar but my young grandchildren couldn't go in without two adult good swimmers with them.
The points program was a game changer. Now I turn in all the OP weeks for points and use them for gold season. You might ask who wants to go to Florida in the summer months. Well you'll be right if you were going to central Florida, Orlando for example. It's hot, sticky and not much of a breeze. OP is hot, breezy cool, humid but you don't notice it because of the ocean breezes. The surf is warm and gentle, fine for young kids and adults who are not comfortable in rough surf. On top of that it's much cheaper point wise to go in summer rather than the seasons I own. As an example I turn in my 3bdm silver for 4225 points. I then reserve a 3bdm in July but it only costs me 3675 points. I turn in my silver 2bdrm OF for 3825 and use it at MFC in Feb for 4125 points. That costs me 300 points but really, 300 points to go to MFC in Feb rather than OP in Sep, that's a no brainer. With my 3bdm swap I'm still ahead about 300 points.
As far as beach conditions OP in Gold season is the best choice in my opinion.