Hi there local sailor,
I like your way of thinking. Heck, we sail year 'round in this area, and it wouldn't be like you had to work the sailing into a "short" sailing season. Give up the job, and then you really can make sailing time. (Laughing Out Loud).

The way I see it, they haven't built (personal opinion) a perfect boat yet. So, the more you have, the closer you can be to the perfect boat.

The windsurfers and kite sailors have already figured this out. Although it is a bit simpler for them to bring all the toys to the beach at the same time. You would probably want to do this to make full use of the different wind conditions.

I can try a bit of logic on my wife when I try to pull this off:
The insurance company would probably extend a discount for multiple policies; my property value would increase by building a new structure to house this (these) additional boats;
she wouldn't feel obligated to help me hold the boat down when conditions were less than favorable for single-handing; AND the sails, rigging, and other assorted "boat stuff" [that I usually replace every year] would last longer (because I would not be using one boat exclusively).

If I have a problem getting a seal of approval, maybe you can help me with my close.

Stop by and say hi at Dunedin. I'm there almost every weekend. One boat (P19MX)
Dave