Screamer, sounds like a great place for sailing, but not everyone is so well situated. Also. 50-100 days sounds like a lot, but thats 1-2 per week. If they don't occur on weekends, or whenever you are off work, then your odds of getting a good shortboard session are 1 or 2 in 7. A "losing streak" could go on for weeks at a time.
I sail both long and shortboards, and for different reasons. Sailing a longboard, is sailing w/o the expense and hassle of owning a "real sailboat." Its also a lot faster, and IMO, more fun than a sailboat. Sailing a shortboard seems more like "surfing", but can be done with or without the waves cooperating. You don't even need an ocean - a lake or river will do. All you need is wind - and a fair amount of it. But neither shortboarding, or longboarding is for everyone. In this sport, longboarders are a small minority, though hopefully one that will grow.
It will be interesting to see if the longboard revival is for real. I live in a place (inland SE US) where light winds prevail. If anyplace is a longboard haven, it should be here. Yet few local sailors are sailing longboards, now, and its been that way for the more than 10 years I've been windsurfing. James' story is sort of similar to mine. I started out on longboards, and gave them up more from frustation than anything. (Couldn't to get into the straps, hard to get planning sometimes, difficult in high winds etc.) I went to wide formula boards, hybrids, big sails, etc and even sold my longboard. Along the way, I got into conventional shortboards from 84 liters on up. Last spring I bought an old (1987) Mistral longboard. Soon found out that my longboard sailing had improved greatly, even though I had been sailing different types of boards. I got back into longboards in a very big way, racing, and sailing in winds light and strong. I eventually got a Serenity. Now I sail it in non-planning winds, and switch to one of my shorter boards when planning is possible. My thinking is to get the best ride for the conditions, and sail as much as I can.