Hi Vince.
Been through the same myself.
Started with a C-22. Had no idea how to sail and what was what. My pilot experience helped a bit, after all, wind is wind!
Ha.
Well after about 6 years, 6 years worth of dock rental, upgrade from hanking to furling and the normal wood work and up keep, I dreamed of bigger.
Bought a 1977 C-30 and spent 12 years (with the help of MANY on this forum) and thousands of dollars and hours keeping her (and me) happy.
This last summer, I spent 3 months stripping her topsides down to nothing, drilling, sanding, filling, more sanding, more filling, painting, more sanding, more painting, her topsides were a thing of beauty.
Murphy's law hit me and I am in the middle of a hidden crack/hole/breach in the Atomic 4 and am fighting some type of water leak in the crankcase.
I will fix that, hopefully before spring. And I will sell her.
But enough is enough. I started thinking about the struggle to get in and out of the water at age 58, the contortions of upkeep on a soon to be 50 year old boat and starting dreaming of bigger.
Just finalized purchased on a Catalina 380. I looked at the C-36, but for some reason the aftstateroom just appealed to me over the C-36.
So my journey is nearly complete. From the perfect size and transferability of the C-22 to the "I am a yachtsman" size of the C-30 with it's HUGE interior, galley and REAL head to my 'final' stop at the C-380....
But you're not really a boat owner till you own something over 40', right?
Some day....some day.
I wish you good luck!!!!!
Chris