Yes, for sure. I think hikers and backpackers and back country skiers do too. I think it’s natural to sit and mentally war-game all the things that might go wrong on the water. And since people don’t have to rely solely on their own skills and resources all that often, they tend to overthink it. It’s also a very gear centric pursuit and the variety of different boat and gear combinations is endless. And the internet.
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Are you overthinking overthinking? 
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I know I have over thought many things. A small example is this.
I was thinking about a travel paddle and after making a paddle that was 4 piece , but with an adjustable loom. I found that the adjustable loom made it so that the four pieces were no longer all the same length so didn’t fit nicely in a suitcase for air travel.
Looking at the end result I decided to see what would happen if I did want to carry an adjustable loom and I decided to see if it would work. That is why you see the loom section on the right. I made it so I could add this loom section into any 4 piece and it would work.
I don’t really need an adjustable for travel…but over thought and was curious about weight and balance of the finished product.
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Has been a common practice. Obviously as fewer boats ultimately get sold, the stock of demo boats on a lot will diminish.
This is the way. When I was a new paddler I was shy about asking and would not have done this. Instead I bought whatever inexpensive used kayak I could and paddled it until I decided I needed something else. Now whenever I have the chance, I try out other people’s kayaks.
I think one of the hints that someone is a more serious paddler is their willingness (eagerness!) to take you up on offers to try your kayak or to trade paddles.
And happily I’ve found the vast majority of experienced paddlers to be incredibly generous with their gear, their time, and their advice.
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Some over-think and some under-think.
You see plenty of under-thinkers in their ill-fitting big box boats out on waters where they ought not be, and without a pfd. Whether you choose to call them “kayakers” or something else is another discussion.
On the other hand, the over-thinkers tend to end up here, where we can share our over-thinking with other over-thinkers. 
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Think the more experience we gain, the more educated we become, the more we grow within our sport, what may be considered overthinking is actually the norm.
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Perhaps it is possible to do too much off-water research. It is important to learn certain things about your next kayak, such as length, weight, cockpit size, hatches and whatever else matters to you. Many years ago, when I still had a big heavy sit-on-top kayak, I joined the local Appalacian (sp) Mountain Club and went on their paddles. I met lots of nice people who were willing to share their thoughts and let me try their boats. I have since tried several boats, starting with a Pungo which was tough and comfortable but then became too heavy. Now I am 84 and just love my latest boat, a Current Design Kestrel 120 - perfect for me! Keep trying new boats!
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Well, I’m in Fort Worth and West Side Boat shop is long ways away for a test paddle 
Yes, I want to get out and test paddle a few different fast boats and learn just how skinny I can go before it’s not fun anymore, but it’s hard to find those types of boats near me to test paddle.
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I highly recommend seeking out one of the QajaqUSA skills camps, which are offered at various locations around the US annually. If you can swing the time (usually a 3 or 4 day weekend) and cost (about $75 to $100 per day) you will not only get excellent one on one coaching in paddling skills, rolling and rescue (self and assisting others) but meet some great folks AND get to test out dozens of different sea kayaks. The organization provides a number of skin on frame Greenland style kayaks in various sizes and styles but the attendees bring their own boats – in my experience with several of these get togethers, more than half the 50 to 80 attendees bring a range of “conventional” touring and sea kayaks, mostly fairly high performance (Valley, SKUK, Rebel, Tahe, Current Designs, P & H, etc.) And I have found that most fellow students and instructors are gracious about letting others test paddle their boats from the beach at the events.
I’m not certain where all of the QajaqUSA sanctioned events are – there are some on the East Coast, at least two in the upper Midwest (Michigan and Minnesota), and one in Florida. There are other organizations like SSTIKS on the West Coast which also sponsor gatherings.
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I hear you. We don’t always get to test paddle the exact boat we have our eyes on. In general, though, one can get a feeling for different types of boats roughly within the same class as each other and then compare the different classes.
I’m very fortunate with WSBS kayaks. Most people I talk to know exactly what they are and what they can handle, or we can usually figure out the next logical step up based on the skinniest/most high-performance kayak they’ve paddled to date.
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https://qajaqusa.clubexpress.com/content.aspx?page_id=22&club_id=349669&module_id=374924
here is a list of the sanctioned events, but the dates are not {to my knowledge} finalized and some of the sites are moving.
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