Outside the Gate is a COMPLETELY different issue. While it can be blowing 25-30 inside, it's usually less windy outside, except that depending on the weather, the seas can be what will get you. And this is true all year round, regardless of "traditional" weather models that state that (usually) during summer a big high pressure system maintains itself off the coast. Well, not this year, for example. It rained yesterday and today, which means the high dropped south allowing low pressure to move in from the north. What happens as the lows move east are two things: winds increase and because of the low the seas are built up. NOT fun sailing. We've tried to sail to the Farallones twice this past twelve months, in nice weather, and have been turned back both times because of the high seas, even when we planned on good weather based on the forecasts.
I always recommend that folks buy, read and study Kimball Livingston's Sailing the Bay, a great book that explains just about everything you need to know about sailing around here.
Our C25 had hank on jibs, the C34 has roller furling, but I still switch jibs. Even though we have a ProFurl which will allow jib reefing, I tend not to like to do it.
I don't understand the "mainsail from a J24 for a jib;" is it a jib?
Same sail selection for outside and inside. You reef the main in the Bay and pop it up if it's less windy outside.
I will see how it goes in winter.