I know many people here have multiple boats for different purposes, but how many not-right-for-you boats did you buy, and then sell, or keep for another purpose, before finding your current ride?
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Iāve sold a few that I didnāt realize how good they were till they were gone.
Fortunately I was able to buy a few of them backā¦ 
There must be some country songs about getting your dog or truck backā¦
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My first canoe was an old Bluehole OCA Royalex tandem that I set up for solo whitewater. We also used it as a tandem lake canoe. But it was a heavy beast and didnāt work all that well for either solo whitewater or tandem flat water so I sold it and we bought a Wenonah Odyssey Kevlar big water expedition tandem and a Clipper (Dagger) Genesis Royalex solo for whitewater. Sold the Genesis when I moved across the country but kept the Odyssey and still use it for lake and big river travel.
But I also purchased a fast solo flat water cruiser, a tandem whitewater expedition canoe, a solo flat water expedition (partially decked) canoe, a solo freestyle canoe, and a solo tripping canoe. I sold the tandem expedition and solo expedition canoes because they didnāt get used much anymore.
Each of those canoes are the right canoe for the right conditions but If you can only have one canoe it should be a boat that fits the conditions that youāre most likely to paddle.
Tom
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One I bought several years ago and got rid of a few months ago: Epic V10 Sport - Iām just not a āfastā paddler. (I still have and infrequently use an Epic 18X).
Have been through a number of sea kayaks in my paddling life.
My current āright oneā is the composite Petrel Play.
Not exactly a ārealā sea kayak at 14feet, but it does all I need it for - short daily paddles (10miles), weekend long paddles (45miles), surf, itās a fun boat. I donāt think Iād use it for long trips
No such thing the search never ends 
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For kayaks, I found the right one on my second try (CD Caribou), which I still have 20+ years later. I added a BBK Recluse to the fleet, which I eventually sold, and went with a Valley Anas Acuta, which I wonāt sell. Compliments the 'Bou nicely.
As to canoes, my second one was an Old Town Penobscot 16, which is a great boat, but not quite what I wanted for solo paddling after a few years. Since my better half swears sheāll never get into a canoe again, I got a Bell Yellowstone Solo. Very nice solo, but now Iām leaning towards a Bell (Or Northstar if new) Magic. Demoed one and fell in love. $$$ is an issue at the moment, so the Yellowstone is my canoe for now. I really like it, but still feel there is one more step eventually to find what I wonāt sell (Yeah, right).
plenty of not so right boats, perception mirage k - seat to hard, not enough rocker (pearls out when surfing), Lettman k not conducive to hitting rocks (too much time patching), phoenix slipper k too much time patching and uncomfortable seat, flashback c too wet for class IV water, several perception and dagger c1s (all became too uncomfortable as I aged), wavesport y too wet a ride and too small a cockpit, pyranha shiva k too hard to roll and could not get a good fit, wavesport diesel k too hard to roll a little squirrelly in big water, mr adventurer canoe- too heavy, difficult to portage, taureau oc1 too tippy (had to raise saddle way up as knees went bad) and taureau was too short- couldnāt attain at all, made it difficult to catch features, paddling pools was a chore, Liquid logic XP k- too big, too heavy, to hard to get a good fit.
Current ride pyranha 12r k- no such thing as a perfect boat- itās too heavy, even though it is 12 feet you still have work a bit to make it track straight but it does make the pools more enjoyable than my shorter boats, and the narrowness helps my roll.
Favorite boats overall: mr explorer c, mr m.e. c, perception gyramax c1, wavesport diesel k, worst boats: taurea oc1, slasher c1, a slalom racing kayak I bought used, shoshone raft, aire tributary duckie
I have owned 5 canoes. Three were outstanding boats , a Malecite , a Rapidfire, and a Voyager but Iām apparently not a canoist. Two I built from plans. Sold one and donated one.
My first kayak was a Perception Acadia. It was just too small for me. My son has it now. My second was a Necky Zoar. It was a too big for me and I knew nothing about sizing cockpits.
I have had four WS Tarpons. Three were 160 . Two were the old style which guaranteed you would be sitting in a puddle all day. I still have one that is my go to for just about anything. It has gotten too heavy for me to comfortably handle but my grandson is a wannabe fisherman and loves it. I also had a 140 .
I was given a Pungo 120 but it was too small so a relative has it and I have a 140 which is a great boat for swamps and rivers.
Then I started on lighter weight boats. Had a Carribean 14 and have a Skimmer 14. I donāt like the way either paddle.
I also had A Stellar S18S surf ski. Iām not a ski guy.
To be fair, I have two issues that have heavily contributed to going through so many boats. I am tall and heavy. I think if I were a bit shorter, there would have been fewer boats.
The other is a back that is an arthritic disaster. Even moderate comfort is hard to find in a kayak.
Finally, I have a newly acquired S14S that I havenāt paddled.
Any normal person reading this , and the other responses, probably thinks weāre nuts. As a vice boats arenāt too bad. A lot cheaper than cars or wimmin. Those are long term commitments.
I forgot my first canoe , a Sawyer tandem, and the first kayak, a Folbot Super built from a kit.
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Several is the answer. Thatās why it is often recommended to buy used initially (so you can test and resell at approx the same price as you purchased) unless you just won a megaball lottery.
At least in my case, it was a matter of learning to paddle, learning how a kayak is supposed to fit, and figuring out what boat handling characteristics I wanted in the water conditions I normally paddle. You are lucky if you live near where there is a vibrant sea kayak community so you have more options to test drive.
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I have had about 7 canoes, one kayak which I built, 2 rafts, 2 drift boats and several sailboats.
I lucked out because my first canoe was a Sawyer Cruiser. I have only bought good canoes after that. Now I am down to one OT Guide 18 in cedar and canvas and one OT Canadienne in kevlar. Very different but excellent canoes. The search is over.
Lounging canoe-
OT Penobscot 164 plastic > Wenonah Jensen 17 fiberglass > Wenonah WWII frankenboat kevlar (still have this one)
Racing canoe
Wenonah Stock racer 16 > Crozier J200 (still have)
Surfskis
Epic V12 > Stellar SR gen 1 > Fenn XT gen 1 > Fenn Swordfish S (still have) > Ozone Vega (next on my list)
So my answer is 2, 3, and 4 (thinking about #5) boats to get to the end of the journey
I have changed kayaks (and sailboats) more because my needs have changed rather than because of the boat itself. I think the only kayak that I really wasnāt super fond of was my Valley Etain 17.1 - it was a little too small for me and very awkward to carry solo (unbalanced and heavy) so it just wasnāt user friendly.
Iām very happy with the fleet I have now - a Dagger Stratos 12.5 S that I keep at the marina, and a Valley Gemini SP (rotomolded) and a Tiderace XCeed S. All are great kayaks that do what they are supposed to do very well. I probably wouldnāt own something like the Dagger except that my needs for a kayak to keep at the marina are very specific - a short boat (<13ā, to fit on a rack in my slip) that is capable of handling open water, since Tampa Bay and its 9 miles of fetch are right at the end of the channel.
I have a lot of boats around here, but less than Iāve owned. . None of them are/were perfect. Somewhere around 15 1/2 over the last 50 years. One is still under construction.
Still looking for āthe right oneā.
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Iām super happy with my little fleet of canoes, six solo and one tandem. About 20 have come and gone before them over several decades. There are a few more Iād consider if a nice one popped up nearby used at a good price. This one is tempting, expensive yet a bargain.
What do you mean right ONE? For me, itās right ONES.
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āIf you canāt be with the one you love, love the one youāre with.ā
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Hereās more detail than you probably want to know. Over the past 20-25 years, I counted up that Iāve owned 23 kayaks. I currently have 8 that are split between two houses. That leaves 15 that have moved on. Of those 15:
4 had things that I disliked enough that I was unlikely to use them any more
5 were sold in the process of upgrading and they also had minor things that I didnāt like
4 I liked but sold to upgrade none the less
2 were bought cheap just to resell and make a few bucks
I need to thin the current herd of 8 kayaks, but there are no clear losers among them. They all serve a purpose from paddling creeks, bashing rocks, serving wife or friends, and general touring/cruising.
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On the contrary, those are exactly the details I not only want to know, but relish reading.
The 8 still in the herd better all step up their game lest they get thinned.
We have 3. Iāve already sold 4 that we used to have. I want one more, plus I want to swap out one of the 3 we have. But thatās just for NOW.
(Iāve only been kayaking for a few years though so I need time to catch up.)
Wow, that is a beautiful boat!
I figure that each of the five kayaks Iāve purchased was the right boat for me at that particular time. I learned from each one and am still learning from the last one (CD Prana LV).
The only one I disliked was my first, a Necky rec boat. I had never paddled before I bought it but was able to learn the fundamentals of the forward stroke as well as what I didnāt like, so it wasnāt a complete loss.
I still have three at home, enjoy paddling each one, and paddle two regularly. The 14-footer needs a backband replacement. Once thatās done I can do some river paddling.
Now, if a 21" wide, 15-foot long skegged kevlar kayak came across my radar, Iād defintely go for a demo paddle. 
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