As my post # 16 intones... I understand your position completely!
It's been a long road.... or waterway rather.
My very first boat was a Cajun 19' center console that my father bought for me for $1200. It had been sitting under trees rotting for 6 years, it was filled with at least 6 lawn bags full of wet leaves, and the motor had been sitting on the skeg for who knows how long. It had good compression though and we thought we could get it running again. We took it home and cleaned it up and spent time and a few bucks and got it running smoothly and reliably again.
When we sold our sticks and bricks house and moved full time into our RV down on the bay, I quickly realized how inadequate I felt with all the large sail boats and cruisers around. We also wanted something more comfortable, so I sold the Cajun for $4600, and we took a few thousand from savings and made a cash offer on our second boat, sight unseen. It was a 2002 Chaparral 183ss and the asking price was well OVER what we offered. Surprisingly though, the seller accepted our cash offer and we drove down to Corpus Christi to pick it up.
There was, for a period of about 4 months last year where we were two boat owners. I picked up a little 1981 Hunter Cherubini for a song, and started refurbing it. It didn't take us long to realize that we were NOT sailors though, so I sold it for exactly what I bought it for.
And then last July, while cruising boat porn on the internet, I came across an ad on yachtworld for my current Chris Craft. The owner was looking for a smaller boat on a trailer that would fit on the boat lift in the back yard of his new home. Luckily I had the Chap, and he liked it, so we traded boat for boat, and title for title. And that's how I ended up owning my Commander, which I love dearly.
Hopefully soon enough we'll end up in a real diesel trawler and have the ability and range to cruise the gulf coast via the ICW, but for now, our weekends around Galveston bay are enjoyable, and getting better the more I work on my boat.
So feeling inadequate in my boats has always been there, especially when we have friends with huge expensive cruisers. But I've learned to be happy with what I have, especially now, because I've done SO MUCH work on this Chris Craft.