Not untill I decided to buy another boat. Up till then I was happy

I have never been unhappy with any of my boats. I loved all 3 and STILL do.
Moving to a larger or smaller boat doesn't negate that. I sold the Catalina
because I wanted a larger boat in better condition. I sold the Pearson because
my wife and I wanted to buy something suitable for a family. We bought the C&C
because it allowed us to sail basically for free while planning for a larger
boat. All 3 are stepping stones and have been thoroughly enjoyed. At your age
you may find a 30 foot old boat "enough." That's fine. But as you'll note, many
sailors want more and slowly move up to larger boats. I sailed my first two
boats for 8 years. The 3rd was a lucky fluke. I know people who buy different
boats every few years. They just love saling and owning various designs.
What's the problem?

RB