When I think of an ultimate trailerable boat, I think of one that is under the limit that does not require a permit to go down the road, one that has a mast that can be stepped by the owner and a boat that can be launched and retrieved off the trailer without the help of a marina. The Paceship 26 is over 8.5' long, so requires a permit (legally - and if you don't have one and get stopped, it can get expensive - but they are not hard to get). It does not have a hinged mast step (but you are looking into alterations, but the mast, even if spliced and hinged on the deck, is a big mast to step regularly without the help of a lot of friends, an apparatus to step it (slow) and with the shoal keel and centerboard, one should be able to launch and retrieve the PY26 pretty easily. So, if one wants to trailer each time they use the boat, one that launches, rigs and retrieves quickly and easily, is the boat that will get used the most. Bayfield is a wonderful place to sail. Just returned from there last night. If you put it in the water permanently there, or on a transcient basis, you will use the boat because it is easy to start the engine and cast off and go sailing without dealing with launching and retrieving or stepping the mast each time. There are more expensive marinas and cheaper marinas up there. I know some people who have kept their boat at Port Superior Marina (just a few miles south of Bayfield - and considered one of the more expensive ones around) on a transcient basis all year around and the stored elsewhere (where it is cheaper) and actually pay less than renting a slip out for the whole summer the usual way (not as a transcient). Someone mentioned Ashland and there is also Washburn. They are cheaper (especially Ashland), but Ashland is at the bottom of Chequamegon Bay, which is a long ways from the Apostle Islands which is where everyone wants to sail. Washburn is half way down the Bay, but still a long ways away from the islands and so those marinas have more powerboats in them than sailboats. The most reasonable place to get a boat launched by crane is at the Black Hawk Marina (Kenny Dobson is the owner). He has reasonable slips too, but has been full. He is in the process of expanding his marina, but it is unclear when more slips will be available. The Apostle Islands Marina, right in downtown Bayfield has a lot of slips available for the size of boat like the Paceship 26, so that is a good place to ask for your size boat. I don't think you will find it unreasonable price wize. Since you have a trailer you can store it at home and save their winter storage costs, if you prefer. It is a good place to sail out of and it is close to the islands. If you want more detailed info about Bayfield, then send me a reply and I will be happy to share what I know, which is a ton.