The general rule of thumb when deciding on what size boat to get is to go smaller. 45'-50' is really too big for one or even two people. I know it sounds really comfy and all but it will not seem that way when it gets hard to handle. A nice 35'-40' Hunter / Beneteau/Catalina will be a better experience I believe. Also, you will be able to sell it easier when the time comes. In mast furlers are notoriously jammy. I would recommend a traditional system with lazy jacks and quick reef system so you can shorten sail in the bay. I sail my Hunter 34 in the bay by myself all the time and I have had to shorten sail suddenly when coming from behind Angel Island into the slot. I would not want to have to handle a larger boat by myself.