Practical Sailor is ok. I subscribed for a while. I really like Good Old Boat and I noticed there is a link on this site for a free sample issue. When I was learning to sail, I used the book, "Sailing for Dummies." It was great and I learned all I need to know to get the job done. I have never had a lesson.
I have a Starwind 223 but that sounds smaller than you might want. A Catalina 25 is trailerable and there are zillions out there. It's a great boat with a lot of support from other sailors--the newer the better.
What lake are you planning on sailing?