You actually answered many of your own questions as already pointed out, but I will give you my 2 cents. I have been sailing almost since the earth cooled and started out on a day sailor and gradually moved up into larger trailerable boats that I could sleep on and then boats that I kept in marinas. When young, it's no big thing dealing with launching and retrieving and stepping and unstepping the mast along with the other tasks of trailer sailing. The upside is you can trail your boat to different bodies of water and expand your horizons with those opportunities. The upside of getting into larger boats is more comfort down below and while underway. When you have a boat at a dock, you just jump on board, start the engine, cast off the lines and shore power and head out. No launching. No mast stepping. No parking the car and trailer, etc. Of course bigger boats cost more. You have dockage, insurance and sails are bigger, so they cost more, the systems are more involved (but don't have to be overwhelming) and there are maintenance things to think about. A trailerable boat might not need antifouling paint, but a boat kept in a marina probably does. You can learn to winterize your own engine, if you live somewhere that is done, but check your insurance policy. If something goes wrong, they might not cover the damage if a boat owner does it, but if a professional, like a marina mechanic does it and something bad happens, they usually will cover the loss. With a larger boat kept in a marina, you have more storage cost, but they do the work for you hauling the boat and launching it, etc. if you are in colder climes. In larger boats you have more headroom, more places to put stuff, a more spacious head, usually a galley, ice box, maybe refrigeration -basically lots of comfort that you can call your own and because you have room to keep stuff, you aren't going to be loading and unloading so much with each trip. With a larger boat, you can go out in bigger water and depending on where you are, you can take long voyages. Depending on the boat you buy, most likely you might need more crew, but I know couples who own quite large sailboats that they sail themselves. And, then there is the camaraderie of your fellow boaters at the marina and all that it entails Social events and just fun stuff you do in a marina environment that you don't necessarily enjoy as a trailer sailor. As you age, trailer sailing most likely will get old and you will enjoy the convenience that a larger boat at a dock will provide. Personally, I totally enjoyed my life as a trailer sailor. Now I am enjoying the life on larger boats on bigger bodies of water.