Re: Aspiring sailor searching for boats.
I've never taken a formal class, but have been sailing for 30+ years. I am NO EXPERT, and never expect to be... However, I have still considered taking the classes, I am definitely NOT against it.
The others above (and myself) are trying to help, if you can answer these questions honestly we may be able to point you to some boats that will fit the bill. Keep in mind a budget would help as well, it'll keep us from recommending brand new boat lines for you or boats totally out of what you are hoping for.
Sailing a Capri 25, cheap, fast, trailerable, and paid for... Catalina Mainsheet Capri 25 Tech editor that's large (I mean at large).