What is the boat that you no longer have that you wish you didn’t get rid of?
There’s a few on my list, but the number one is GRB Classic XL.
My last WS Pungo 140
I was ready to sell all of them.
The one boat that fell apart that I would love to have in better shape was a kevlar Sawyer Charger. It was 18 1/2 feet of fast gear hauling canoe. It was long, deep and seaworthy with plenty of rocker for rivers.
I sold 2 kayaks in the past week. I regret that I had to sell them, but the Rockpool Alaw Bach was never going to be a good fit for my body size. And my health doesn’t permit me to paddle whitewater anymore, so selling my Dagger Mamba also had to happen. They were both exceptional boats - especially the Rockpool. They went to good people, which helps.
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That could be another thread, boats you never paddled, but always wanted to. I never had a chance to paddle a Sawyer, but a Shockwave was on the list.
No regrets the two boats I have sold were canoes. I sold a Curtis Kevlar Vagabond great canoe, but too small for me. I bought it so my wife would have a solo, but after a few years she said she enjoyed the tandem better. It was small for me even though I enjoyed it, but paddled my other Curtis canoe when I solo. The Wenona Advantage in tuff weave was great, but it just wasn’t used enough, and a good friend thought it might be good for him so I sold it. Used the money to…Yes… buy another boat, surprise! A small sailboat with a cabin. I have an old Mohawk WW canoe I am not using, but wouldn’t miss, but might use in the future. I passed my Mad River Guide on to my son.
The way to stave off regrets about selling a boat is to immediately buy another… or my method, TWO others. 
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I’ve never regretted selling a boat because I either had the next one or it was on the way.
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Before I moved to Florida I sold a plastic Valley Avocet that was at my parents place in New Hampshire. Since I lived in Rhode Island at the time I could just bring a kayak when I drove up. I didn’t terribly like the Avocet, great kayak but not comfortable for me. A couple of years later I moved to Florida and of course driving three days each way was not feasible on limited time off but can’t take a kayak on the plane! So I had no kayak there at a lakefront house until this past year when I finally bought a used Tempest 165 to keep there. So nice to finally get back on the water after 8 years!
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I don’t regret selling it because it was a means to an end and a smart move but I really liked the way my “Z” paddled in rough water, wind, surf. Sometimes I wish I still had it.
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I ordered a fancy new SUP that I thought would arrive right after I sold my boats. I missed snagging the last one in stock by hours. Now I don’t know when it will be here since the supply chain is still so sluggish. Waaah. I’m currently all over the place on replacement boats.
I should have kept my Old Town Loon 138 and my wifes Loon 100. Currently have a Loon 126 and will keep it if I decide get a peddle kayak. That said we go 70% of the original cost back when we sold the 1999 Loon’s a few years ago.
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I had a Souris River Jensen Solo 16 that I should have kept. I had to purge a few canoes when we moved, or at least it seemed like the right thing to do at the time. 16 feet, 29 pounds and fast. You could see through it but it was a tough boat with their Flexible Rib System. I’ve never seen another one.
I had to smile when I read that. Made me feel like they were puppies.
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Canoes I regret selling; the Dragonfly, and the SRT are the two I most regret.
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Curtis Dragonfly ; an original one.
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Hemlock SRT ; loved that boat.
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Swift Osprey
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Bell Wildfire; in kevlar layup.
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Bell Flashfire; in kevlar layup.
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Wenonah Moccasin
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Mohawk Probe 12 II
BOB
Why would you ever get rid of a boat? 
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Dumping a SOT
Selling a boat means that you can move on to the next one or two.
I have sold 6 canoes, 2 sailboats, a wood sea kayak, a drift boat, and 2 rafts so far. There will be others. The big powerboat is the next to go.
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The Loon 138 would be my only regret, too. Good fast boat for what it was yet you could put anybody in it. All 3 of my kids started in the boat on a foam pad just in front of me because the cockpit was large enough to pull that off.
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