VT Fitz; Saw your comment so am I a wondering if you are trailering your 27?
The short answer is no. At least for now.
The long answer is, in looking to satisfy our bad case of two-foot-otis last fall, to trailer or not to trailer... THAT was the question.
The thrift (a big factor) and ease of being able to finish the season, throw her on the trailer, and find a spot in the backyard was important for us with our 23.5. Thus, we were scouring the ads for the 260, looking for a larger and newer boat, but still trailerable. We are committed to the Hunter brand. But of the three boats we actually looked at over the prior 14 months, none were acceptable. Since other boats will pop up in searching a given range of length, other models appeared, and when we saw how clean Skaði was, the 27-3 we ultimately purchased, we just had to check her out. The rest is history.
The ongoing prospect of coughing up $1500 or so for winter storage for the foreseeable is not the most pleasant aspect of stepping up, but we've accepted this additional financial commitment as the price to play with a bigger keelboat. Besides the stability of a keel versus water-ballasting, having standing headroom down below and all the additional amenities the 27-3 has versus 23.5 -- or even the 260 -- is worth the expense... at least for the next 8-10 years. Hopefully longer.
She's got the shoal wing keel, so only draws 3 1/2', but to now we really haven't considering getting a custom-made trailer. I have the schematics to make a cradle to build on to a trailer superstructure, but then I'd need road permits and such through three states, which I'm not eager to deal with. Also, I'd need a larger truck (my Tacoma was fine for the 23.5, but underpowered for the 27-3 plus a trailer). Clearly it would need twin axles and brakes. I'd also incur the cost for them to sling it on and off and to step/unstep the mast... When it's all added up, I doubt the numbers favor trailering.
But for sheets and grins, how much do you think it would cost to make a trailer? $5,000? $10,000? Maybe it would pay off over 10 years. Might also be an asset at time of sale.