Re: can I afford to continue sailing
This topic interests me as my wife and I (together) made the decision to sell our boat. We both love it. Our daughter loves it. This is our only hobby. It was a very difficult decision. We (again, together) agreed that we would buy a small day sailer that we can trail to the lake, store in our backyard, and still enjoy sailing as a family. We will probably sail more than we do now since we can go to the smaller lakes close by. BTW, our slip fee is just under $3K annually. This is what will allow us to be financially responsible and continue to sail.
As much as everyone keeps telling you that money does not matter, you have to do what is comfortable for you. I find those that say money is not important have plenty of it. Before I got married I used to fly for fun. It got to be too expensive for me. I got into serious debt funding my habit. I made/make a good living as an engineer. My wife was lucky enough to never have been flying with me but still got to pay the bills. After we dug me out of the debt hole I created we bought our boat.
The economy is in the toilet. Jobs and money are getting more scarce. You and I came of age in a falsely strong economy (can we say tech boom and bust). Life is not like that right now.
You are married with kids. While having fun is important you chose the family responsibility. Sometimes you don't get to do what you want to do. Welcome to the real world. I tried doing what I want while ignoring the cost. I am now 10 years behind my peers financially. While they can really afford boats now, I have to sacrifice to many basic conveniences in life to afford it. Living life like you may die tomorrow is the opposite extreme of what your father did. Find a happy medium, be thankful for your family, and find a true compromise so you can still sail, even if on a small day sailer.
If you all think sailing is expensive, try flying.