Here is the problem I see with your plan.
You are trying to get too much out of one boat.
While Seaojoes boat looks like a beautiful boat to sail and camp on for the weekend, I don't see it winning any races. If you intend to race and win you need a boat set up for that meaning new sails, new lines, and maybe a new job. Almost any competitive racing boat I have seen has been stripped below and stuffed with sails. Even up to 41 feet, I have seen little room to sleep or cook.
On racing boats less than 30 feet the boats tend to be tight below but then when stuffed with sails, you'd be hard pressed to find room to even use the head.
A few suggestions around this. Figure out if racing or weekending are more important to you. You could do both but the same boat in the size range you are looking at won't be comfortable and competitive in the same boat. Except maybe the Ericsons or J-92.
If you live near Dana Point I have two solutions for you. Buy whatever boat you want and call me, I can be there 3 days a week so you won't have to single hand.
Join Aventura sailing club. My sailing club in SD is affiliated with it, I wish I had joined there instead as it is closer and the boats are outrageously cheap to rent.