One major aspect of that kind of change is the cost of ownership beyond the actual price of the boat. A Pocketship-class boat can be dry-stored in a garage eliminating marina fees and the yearly haul-out. It has far fewer square feet of surface to clean, paint and varnish. If it's stored indoors on a trailer and only put in the water for a few weeks at a time, expensive and toxic bottom paint is not needed. In fact, if you're willing to settle for a workboat finish, no marine finish products are needed.
As Howard mentions, the on-board systems are much simpler (some non-existent) and therefore cheaper and easier to maintain. Since you build it all yourself, you're free to substitute DIY store hardware and skip the "marine" tax. (Just be careful and stay aware of possible corrosion and strength issues.)
A home-built stored in the garage can also be much cheaper to insure. You can easily justify going to a liability-only policy. If you stay engineless, you don't need fuel spill coverage and in some states you can completely skip registration fees and excise and luxury taxes. Depending on your situation, there may be other savings available, too.
But don't expect to save acquistion costs by building it yourself, especially if you put a value on your labor time. Howard is right about needing to consider if you really want to become a boat builder. Many of the cost and simplicity advantage are the result of having a smaller boat, not a home-built one. You could get on the water for less money and time with something like a used Wight Potter 15 if those are your main priorities while still having the financial and time advantages of a smaller boat.
Howard also brings up the re-sale value. The sad truth is that unless you have done a truly exceptional job of building and maintaining the boat and find exactly the right buyer, you'll be lucky to get back the cost of the kit and supplies used to build the boat. Buyers seem to start with the kit price and then discount because it's a "used" boat. Never mind the additional supplies or the skilled labor it took to build it.
Building it yourself does give you the major advantage of knowing where and how everything went together. I disagree with Howard here in that I think that building it yourself makes you the best possible person to maintain it and makes it much easier to maintain than any factory boat. Factory boats have "invisible" structure. They have changes from one production run to another. They are also often optimized for assembly over maintenance. They use factory tooling and professional tools. The materials come from professional supply chains. Whereas with a boat that you built you know exactly how things are put together (you can even customize it for easy maintenance). You own the tools that you assembled it with so you can do it again, if necessary. And you know where to get the parts and materials.
Another advantage of a smaller boat is flexibility. Trailerable boats can also go places where larger boats can't, like inland lakes across the country or that boat show on the other coast. They can also get to that picturesque sailing spot down the coats at 55 mph instead of 3.
So I would say that if you want a simpler, cheaper, less time-consuming and mor flexible sailing experience, go ahead and move to a smaller Pocketship-class boat either home-built or used. If you have the time, motivation and some extra money and want the builder experience, the Pocketship is a very nice boat.
Have fun,
Laszlo