I can certainly understand your attraction to the Vanguard; to me, the Vanguard epitomizes the CCA-inspired look of a coastal cruiser of that era. To me, it is what a boat should look like. As my wife says, "It looks like Popeye's boat". Although she doesn't mean it as a compliment, I really "feel" the Vanguards/Tritons/Seabreezes, and their ilk. Just seeing a picture of one makes me want to sail away to Block or Martha's Vinyard or downeast.
However, I have to echo something Jeff H said. Although my experience on a Vanguard is nothing compared to his, I did go sailing on one once. The breeze was stiff but not overly so at about 15 knots. Seas were very flat for the conditions, and what with the full keel and (I thought) heavy displacement), I was expecting a stately ride. I was quite surprised when the boat went over on her ear almost immediately. She stiffened up once over, but man, that was weird for me. This boat that I thought monster heavy and full keeled was heeling more than my Catalina 22 (my boat at the time) would be! And talk about weather helm... yikes. I had the owner let out the traveller to the end of its run so I could hang on for more than a few minutes without cramping up. It was a fun, exciting sail, but I not something I would want to have to go thru on a multi-day cruise.
If you really like the look of the Vanguard, but want to avoid some of the pitfalls of the full keel/barndoor rudder, check out the Pearson Renegade. She's smaller (27'), but has a split underbody with a spade rudder and separated fin keel. Above the waterline, she has the overhangs and springy sheer of the Vanguard-style boats. You can get one for about half of your budget, and spend the rest paying someone else to upgrade her for you. Best of luck!