In my well-considered opinion of but a few moments here, it seems the concept of best to worst should be applied by ranking on three criteria--access, close destinations for weekenders, and overall venue quality. So, states with virtually no access to sailing (no suitable waters) also lack destinations and should go to the bottom. As day sailing can be done where ever there is access, that activity in itself would produce a neutral score (i.e., every place would get a "point").
States with only small mountain lakes and reservoirs potentially offer high venue quality but few destinations and limited access over the whole year. Coastal states, including those of the Great Lakes and some that border rivers (e.g., Missouri), have the most overall access and thus, potentially, the most destinations. Venue quality is the variable having the greatest impact on the score.
Northern and eastern coastal states east of the continental divide have less general access than southern ones due to their winters, but can have very high venue quality. Southern states of the GOM and the Atlantic Ocean, and especially Florida's west coast, have year-round access from hundreds of locations, many destinations, and many, many places of high venue quality.
The Pacific coast states offer limited access compared to the southeastern ones due to their rugged coastlines, the exceptions being in the locations of large estuaries; particularly, San Francisco Bay and the areas of Puget Sound/Salish Sea in Washington State. However, there is year-round (i.e., all seasons) access all along the Pacific coast and the venues offered are quite impressive.
For access, destinations, and venue quality--my pick for No. 1 is the Pacific Northwest (Washington); conversely my lowest pick would be land-locked states offering only small mountain lakes or reservoirs, if even that. So WVA would definitely qualify as a low score as would most states of the rocky mountain region and most of the plains states (Kansas, etc.). So if you want to find the very worst, look among those!!