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In different ways posts above are saying the same thing in different ways. At the risk of being repetitive it's my turn :).
Some people are passionate sailors, some are not. Don't make you a bad person regardless of which one you are. Will outline several Outbound owners I've come to know.
1. Gentleman I'm meeting this AM to help me finally, finally gets the rags back on my boat. He and his wife did the SDR three years in a row. This fall taking the year off to hang in northeast and ski a bit. Then back to it.
2. Couple sold the house and cruise. Getting it together to leave here and go to Patagonia. Been on the boat for nearly a decade.
3. Couple of automotive engineers. Did the SDR once. Hated the passage. Boats up for sale.
4. Couple with very young kids. Picked up the boat in China sailed her to Aussie.
5. Couple of 80 somethings we met in national park in USVI. To old to safely run the boat. Hired 40 something Canadian to live on and sail the boat.

Unifying thing is all these folks are or were passionate sailors. Were you ever a passionate sailor? I meet passionate day sailors, coastal cruisers, weekend warriors and liveaboards. It's not about that. It's about passion. There's no relationship between the boat and passion. There is between sailing and the sailor.

Would suggest this year take your ten days all together. Sail some where. Expand your horizon or if you must just daysail every day. If there's passion at the end keep the boat if not move on.
 

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It is a very interesting question that we know that one day we will have to face. People have asked us this question many times. We are 70 years old and pushing it hard. We are currently in Georgia in the Black Sea. It was not easy getting here and be more difficult getting back to Turkey.
But when we get asked the question we tell them a story.

When I was younger I was a climber and member of Mountain Rescue and moved east and helped put a group in there. I was a certified high angle rock rescue member and taught climbing and high angle rock rescue. Every 2 years you have to requal to maintain you certification and I had missed a year or so and I knew it. Eventually it caught up with me and it was realized that I was behind on my cert. So it was set along with a group that was trying to qualify and I was a tester. After the group was finished it was my turn. They set up tests for me and I pulled them off flawlessly. at the end you sit before a group of testers who evaluate your performance and give suggestions for improvement and tell if you pass or fail. The testers do not care about friendship or not but skill and ability to perform. In front of the test panel and several people who there they told me what they thought. They said they wish they had a video of it as it was the perfect performance without one flaw and not one thing any of them could comment on.
I got in the car to head home with my 2 sons who also climb and I said well guys that is the last time I climb. My boys went ballistic as they said dad everyone was watching and commenting on how great you did and were raving about your ability. I said yea but what you do not know is that I was at 100% and if one thing went wrong it was not going to be good. I quit and have not climbed since -- except to climb my mast.

Hopefully I will know when to leave sailing.
 

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my boat costs me $1000/year, for storage, i have a free mooring, and i do all my own maintenance -- i know thats a bargain by most standards, but not sure for me -- i'm 68, fixed income of 45k, no debt, 2 modest homes, good health, and i enjoy my time on my classic pearson triton -- but due to a very full, enjoyable, life on shore, as a musician, i only get out about 10 days per season, which i calculate at $100/day -- i'm guilty of being cheap, its inherited i guess, but i have trouble justifying that expense, when i think of other things i could spend that $ on -- ???
It sounds like justifying the cost is your main issue. If you still enjoy sailing and don't mind working on your boat, then I'd look to start a boat share to reduce / eliminate the cost to you. You have to have confidence in anyone you allow to use your boat, but the right person could have many advantages - cash, keeping an eye on her etc.

I hope you get the solution that works best for you,

Roger

P.S. I don't see being careful with money as being cheap.
 

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One of None
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OP only posted twice which pretty much indicates the answer. The rest is us.... We all be preaching to the choir! Lol
 

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al brazzi
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Yes it looks like he has made his call probably not reading any more buy maybe.. We do get email notifications. Obviously a question we all mull around and its just sailing nature. Interesting the different thought processes we all go through. For me I want to get it right if I'm struggling with a performance boat (like I am now) I will stick with it until I get it "right" then maybe move on. I sailed, got licensed, chartered, then drove race cars for a while, then sailing again. For me it is much easier to move on if I feel like I accomplished something.
 

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OP only posted twice which pretty much indicates the answer. The rest is us.... We all be preaching to the choir! Lol
I got that impression on the 2nd page...LoL
 

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I guess you'd have to gauge how much enjoyment you're getting out of it. It doesn't sound like you're in bad shape financially and the cost isn't crazy high. I know I'd have a hard time giving it up.
 

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As the boat gets older... and the skipper gets older... we sail less but work on her more! hahaha But it's therapeutic and makes the sailing special in a way. If I can't physically sail... I won't. But it's physically difficult.
 

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Now , or when you sell or give your boat away.!! That would be like a dream/goal for some people. 2 houses,$45,000 a yr , free mooring.Why did you tell us that? Get a motorhome and you can tell more people quicker how much you have$$.
I run into people all the time that tell me how much money/condos/possessions they and their kids have(5minutes after I meet them)
 
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