I have actually made money on the used boats I have sold.
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I only consider it making money if the next boat I buy isn’t more expensive! 
Otherwise I consider it “flipping up.”
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Yes, I too have reinvested the profits before.
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Does it count as reinvesting the profits if you buy the more expensive boat before selling the old one??
Of course. The ways we can justify kayak purchases are limitless 
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I try to explain to people entering the sport who balk at the cost of kayaks that you are really just “renting” your boat in the long run due to the high resale value of well kept kayaks…
For instance, I picked up a used Dagger Magellan years ago for $400 as a “loaner boat” (so I could persuade friends to paddle with me). It got frequent use for 10 years before I sold it for $350. So essentially it cost me $5 a year.
My first touring kayak was a new $3300 Feathercraft Kahuna I bought on impulse on my credit card. Got 7 years of wonderful paddling trips on it before I sold it for $1800 to upgrade to a $2200 used FC Wisper (that would have been $5000 new). So the Kahuna only cost me about $200 a year while I had it.
The Wisper cost $400 more than what I got for the Kahuna sale and I have used it widely for 13 years by now, so that is only about $30/yr. I know I could sell it for $1500 to $2000 now since the Wisper is highly desirable with folding kayak fans. That would break down to around $1000 net total cost over 20 years for the enjoyment of paddling two high end folding kayaks. ( Though I am not likely to sell it until I am too old and decrepit to climb into it.)
I can quantify similar cost breakdowns for any of the boats that have passed through or still reside in my ever changing fleet.
Right now my garage holds 10 kayaks and a canoe that would have collectively cost over $22,000 new. I paid less than $8000 for these over 12 years and at least half of the cost outlay came from selling previous boats I had owned and flipped. That breaks down to about $350 a year for the major equipment for an activity I love (add about $100 a year over that period on average for accessories and state permits). I would bet most golfers spend more than that on average per year on gear and greens fees.
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Bought my first kayak, an Aquaterra Chinook, 38 years ago. Thirteen boats later, now in my 80s, I think that my next “kayak” will be a pack canoe. Light weight, easy carry means I’ll paddle more often. And isn’t that what it’s all about?
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So, I considered the cost of $30 a day rental for a sea kayak. I paid $650 for my first one and it came with a paddle. I figured if I used it 22 days, I would be $10 ahead. After that it is money in the bank! 
My first canoe a fiberglass Mohawk Blazer bought in 1974 new for $180, could be sold for more than that now. I haven’t sold that one, but of the 5 boats I have sold I have made $700 above total cost or about $140 each. Yes, that has gone back into other boats. I now consider my used boats as savings accounts earning interest over time. 
How’s that for positive justification of used boat purchases.
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I believe that is a form of speculation based on an economic forecast.
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I bought a 32 pound solo canoe (vintage Curtis Lady Bug) 4 years ago with that same future prospect in mind. Lighter and smaller, and a lot more graceful to enter and exit.
I’ve been looking at the Placid Spitfire (20#) and Swift Cruiser 12.8 (24#). I’m going to need to decide between the two without actually paddling either one and they’re a bit pricey at around $3,300 plus shipping. Tough call.
Can you paddle either? That’s a chunk of change.I know because my least paddled boat was close to that.
Even when buying new, the cost can be pretty reasonable, as Willowleaf said, but I can give another example.
In 2014 I bought my first kayak new, a Wilderness Systems Zephyr. It was on sale, 20% off for the boat, paddle, and PFD. The boat cost me $1,215. Four years later I sold it for $850. So the net cost to me was actually $365, and spread over 4 years, that works out to $91 per year.
That is not bad when compared to renting. And I think I do a lot more kayaking with my own boat than if I had to plan and arrange rentals.
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Greg’s point on saving over rentals is another factor (in investing in your own boat) and is also the reason why I have always owned folding kayaks (as well as rigid ones.)
I like to travel, and if you have to rent a boat at your destination there is not only the cost (as much as $100 a day) but limitations on the type of kayak and the time frame required to obtain and return it as well as restrictions on where you can use it.
You can book a guided trip, of course, but that can cost $200 or more per day. Having your own kayak and personal gear that can fit into a checked bag for airline or train travel and be transported or stored inside a rental car at your destination really allows you to optimally use your travel time and explore where and when you want to venture out.
I joined a friend 6 years ago for a weeklong trip when she swapped her timeshare on the Atlantic Coast for a condo right on the north shore of Lake Tahoe (the complex had its own dock). I originally planned to bring my two lightest folders (Pakboats both under 30 pounds) and kit for them but decided not to. Really regretted that choice. Our only option for paddling nearby was to rent bargelike SOTs, which we did for a day. The cost of the rentals ($60 each for a half day) exceeded the extra baggage charge ($100 round trip for 2 bags) it would have cost to fly the folders there and we could have kept them on the deck of the condo, which overlooked the beach, and launched every day or carried them to other locations around the lake (with the inflatable Malone roof rack system I carry with me) on the roof of our rental car.
I only paid a total of $1500 for those two pakboat kayaks (one used and one a factory demo). With a modest daily rental average of $75 for a decent touring kayak (link below to the typical rates by a west coast outfitter), that would be the cost of 10 days for two people of rentals. Not to mention that you can eventually resell a folding kayak – rental is just money down the drain, other than the memory of the experience provided.
Even figuring in $50 roundtrip excess baggage charges (which don’t always apply – I flew round trip to the UK with my whole kit within the free allowance), if you only use your folder once you more than break even on what a rental would cost, not to mention hours of hassle dealing with getting and retuning a rental boat.
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I’m back in the market as my shoulder heals. I had a Gulfstream years ago, it’s a boat I know fits me!
I don’t understand your comment about the seat? You can’t see the seat in the picture, or is that a modification that you planned to make regardless of the condition of that boat?
I dated myself with $30 daily rental fee for a sea kayak. My how time flies and money deprecates.
$ also depreciate.
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Spouse always laughs at me when I tell him what I’m going to try to get for the latest “we’re-done-with-it” boat. Then I tell him it’s to finance HIS next boat, and he stops.
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