You mention trailering, is the
boat going to live in the
water or on a
trailer?
The 27 was clearly not designed for trailering, as it’s a couple inches wider than the
legal limit of 8.5 ft (in most states anyway). Standard
draft of 4 ft is also a lot for
ramp launching, though looks like there is a 3 ft shoal
draft option.
If you are keeping in the
water for the season, towing it to and from the lake each year is probably doable.
The 22 and 25 on the other hand are both narrow enough for
legal towing and available with swing keels that are raised for towing/launching. Montana means mountains right? What’s you tow vehicle? The 22 is half the weight of the 25.
If you are going to camp on shore, I would consider staying small. You sail from the
cockpit, not the
cabin.