A smaller boat would be easier to own and cheaper to maintain than the 38' boat I have now, but what does it do for me?
In my case and sailing area, a smaller boat presents bigger challenges on the water. My sailing is and will be for some time, more than day sailing. I crave the adventure an ample sailing ground like this delivers. And my area of this vast coast is a bit too big and open for a day sailing only boat. Power boating doesn't provide the sailing we crave.
I would quickly feel like I've used up my sailing grounds if my range was lessened here(I've used up areas before, a large lake after some years, and areas of the coast I've kept a boat for longish term). The smaller boats range and my increasing age would result in a smaller and smaller sailing area.
So the challenge for us is to become more proficient sailors as we age and stay healthy. Sailing will require some physical stamina, always, but that's a good thing for me, as long as I can do it.
I'd still gladly sail a smaller boat, but I may need to put it somewhere more suited for it's use(a trailer may be the best option there,...full circle). We'll still adventure, with a travel on bag.
I have no interest in power only, sailing is the main reason for me to own a boat.