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Hi Eric: I sail out of Long Beach CA. The main thing here is Catalina Island about 20 miles offshore. The crossing can be slow and boring, (motoring all the way) or it can be really scary with high winds and heavy swell. Most of the time it's just about perfect and all year long. If you don't like the open sea you can get lost inside LA Harbor, which is huge.
Anyway...I started sailing years ago in a small trailerable sailboat. Many of my best memories come from those good old days. Some of those mid-70's trailer boats can now be scooped up for a few hundred dollars. With their shoal-draft or retractable keels they are great for lakes. Self-righting and positive foam flotation makes them safe on the ocean as well. The old MacGregors (with their planning type hulls) were fast, manuverable and easy to sail. (They'll give you a real pounding though in a chop).
I have sailed to more places, both lakes and oceans in a trailerable sailboat, then I will ever get to from the slip. It is a lot of work though... When you get to the end of the day, your real work is just starting.