Adam,
First, we all want to encourage you to get out there and sail. But as the old adage goes, "Make haste slowly."
The big flaws of your first plan were:
- You'd be rushing into the boat with little money, then hoping it would not have major problems on a coastal cruise of some four hundred nautical miles, as the divider walks. A week is not enough time to shakedown a boat, verify the reliability of all essential systems/gear/equipment, (not to mention actually become familiar with it all. A week is barely enough time to provision for a trip like this. It would be taking a shot in the dark.
- Speaking of experience, your thin sailing resume, esp. lack of experience in rough weather/foggy conditions, means you could get in way over your head quickly. I especially wouldn't want you to have engine trouble as a relative novice, 'cause even in good weather, it ain't no fun. I can sail into an anchorage and head up, drop my anchor, fall back on it and set it with my mainsail, and I can sail off my anchor in the morning if I have to without an engine. Can you? But that's the easy trick, and many, including myself, consider it simple good seamanship: try sailing up to the dock at a marina with summer traffic all around you, or doing it with the dinghy lashed to your quarter w/ your buddy in it providing the propulsion with the outboard.
I've done all of that, but if I hadn't had considerable experience beforehand, any of that would have been disastrous, except that I wouldn't have known what to do and would have simply sailed to the mouth of the nearest channel, heaved-to, called to be towed in, and paid through the nose for it. Not that you're not a bright guy, but "stuff happens," and when it happens out on the water, you'd better know what to do. New yacht/new sailing ground/little experience is a bad recipe.
Your Plan B is much saner. I think it's far wiser to take your time, become familiar w/ the S Diego boat market (which is huge), begin studying about different sailboat makes and their (sometimes debatable) abilities, all the while saving every penny you can, because if you buy, let's say, a 25ft. boat for 5k, you will just be beginning to invest in it to prepare it for more than day sailing, and it seems you have cruising ambitions.
Not a bad idea to try be economical by dry-sailing from a trailer, though rigging-launching, then recovering/de-rigging adds about 2–3 hours to every outing, excluding towing (and towing problems). You'll still have to have a place to store it. I used to splash my 22-footer in June and keep a slip for three months in the summer. Worth it in my case, because it increased my hours actually sailing ten-fold: I sailed more in the three summer months that I ever did the first year when it was on the trailer year-round.
I won't comment about the ability of a trailerable boat with a retractable keel being able to coastal cruise, but many have done it. Check out
The Trailer Sailor - Home, and John Vigor's book
Twenty Small Sailboats to Take You Anywhere
Now, you won't have standing headroom, but for the cost-conscious cruiser looking to log hours, a trailerable is an attractive way to go.
Fair Winds,
Jeff